DESC:Accordingly, the present invention provides a novel dihydropyrimidine anticancer compound of formula I and derivatives, intermediates thereof and process for preparation thereof.

wherein each substituent is selected independently
R1 is

R1’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’ is --H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R6’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

is single bond, double bond;
R2 is

,
wherein each substituent is selected independently
R1’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

R3 is –CH3, -C2H5, –O-CH3, -O-C2H5

R4 is ,
R1’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4 is substituted naphthalene ring
R1’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R6’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R7’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

R4 is substituted naphthalene ring
Ra is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rb is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rc is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rd is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Re is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rf is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rg is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
The present invention also includes various compounds that fall within the scope of the compound of formula (I). The compounds of formula (I) are illustrated herein below at Table 1.
The compounds of formula I may include but are not limited to the following compounds as presented at Table 1:

Table 1: Exemplary compounds of present invention
Compound No. Structure IUPAC Name
1001
ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1002

ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1003
ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1004

ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1005
ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1006

(E)-ethyl 2-((4-(dimethylamino)benzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1007
(E)-ethyl 2-((4-fluorobenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1008
(E)-ethyl 2-((4-hydroxy-2-methoxybenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1009
(E)-ethyl 2-((2-methoxybenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
1010
(E)-ethyl 6-methyl-2-((naphthalen-1-ylmethylene)amino)-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

The compounds of the present invention include but are not limited to:
1. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
2. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
3. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
4. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
5. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
6. (E)-ethyl 2-((4-(dimethylamino)benzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
7. (E)-ethyl 2-((4-fluorobenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
8.(E)-ethyl-2-((4-hydroxy-2-methoxybenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
9. (E)-ethyl 2-((2-methoxybenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
10. (E)-ethyl 6-methyl-2-((naphthalen-1-ylmethylene)amino)-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

The present invention also discloses process for preparing the compound of Formula (I). The compound of formula (I) may be prepared by the following general schemes described herein below

Compounds according to formula (I) can be prepared by the process illustrated in Scheme-I & Scheme-II
Step-I

Step-II

Scheme-II

In the present invention scheme-I, the catalyst may be selected from the group comprising p-toulene sulphonic acid monohydrate (PTSA), hydrochloric acid (HCl), Sulfuric Acid (H2SO4), Citric Acid, Alumina(Acidic), thionyl chloride(SOCl2), DMF/NaHCO3,Ionic liquid and silica sulfuric acid, acetonitrile(CH3CN),acetic acid(CH3COOH), Zinc chloride, Aluminium trichloride, aluminium trichloride and potassium iodide, Ammonium acetate.

The solvent may be selected from the group comprising 1,4 Dioxane, Acetonitrile, Ethanol, DMF, Toulene, Benzene
In the present invention scheme-II, the acid may be selected from the group comprising hydrochloric acid, hydrochloric acid (HCl), Sulfuric Acid (H2SO4), Citric Acid, Alumina(Acidic), thionyl chloride(SOCl2), DMF/NaHCO3,Ionic liquid and silica sulfuric acid, ,acetic acid(CH3COOH), Zinc chloride, Aluminium trichloride, aluminium trichloride and potassium iodide, Ammonium acetate

The solvent may be selected from the group comprising 1,4 Dioxane, Acetonitrile, Ethanol, DMF, Toulene, Benzene.
The compounds of the present invention comprises its pharmaceutically acceptable salts, hydrates, solvates, crystal forms salts, stereoisomers and individual diastereomers thereof, individual diastereomers, pharmaceutically acceptable carrier thereof and may be used as as anticancer agent.

In order that the invention described herein may be more readily understood, the following examples are set forth. It should be understood that these examples are for illustrative purposes only and are not to be construed as limiting this invention in any manner.

All the chemicals, reagents and solvents that are obtained from commercial sources and are used without purification. The progress of reaction is monitored by Thin layer chromatography (TLC) using Silica Coated Aluminium TLC plates (TLC Silica Gel 60F254, Merck, Germany) by different eluent systems. The spots are visualized by keeping the dry plates in iodine vapors and in UV light. IR spectra are recorded on Perkin-Elmer Spectrometer (RX-IFTIR) scanned in KBr discs and wave numbers are expressed in cm-1.1H NMR spectra are recorded in DMSO-d6 on a Bruker Avance II 400 MHz NMR spectrometer and chemical shift (d) values are given in parts per million (ppm) relative to tetramethylsilane (TMS) as internal standard. Splitting patterns are designated as s, singlet; d, doublet; t, triplet; q, quartet; dd, doublet of doublet; m, multiplet. 13C NMR spectra are recorded in DMSO-d6 on a Bruker Avance II 100 MHz NMR spectrometer and chemical shift (d) values are given in parts per million (ppm) relative to tetramethylsilane (TMS) as internal standard. Mass spectra are recorded on JMS-T100LC, Accu TOF (DART-MS) and Expression CMS (ESI) mass spectrometer. Elemental analyses are carried out with Elementar Vario EL III elemental analyzer. Molecules are given their known names, named according to naming programs within Chem Draw 8.0. All the melting points were determined by open capillary method and are uncorrected. Microwave reactions are performed at 300W in the CEM Focused Microwave™ Synthesis System.

Example 1: Method of preparation of Ethyl-2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)1,2,3, 4-tetrahydropyrimidine-5-carboxylate (I) (1001)
illustrated in Scheme-I

Conventional Method: 4-oxo-4-H-benzo[h]chromene-3-carbaldehyde (0.01 mol) is reacted with guanidine hydrochloride (0.01mol) and ethylacetoacetate in presence of p-toulene sulphonic acid monohydrate (PTSA) (7-10 mol %) as a catalyst in 1,4 Dioxane 30 mL is refluxed for 8-9 h. After the completion of reaction, the product ispoured in cold water, filtered, washed with water, dried and was recrystallized using ethanol-acetic acid (2:1). This process yields the final product 1001 and yield is 60%

Procedure B (under microwave-assisted solvent-free conditions):

Microwave Irradiation Method: The reaction of 4-oxo-4H-benzo[h]chromene-3-carbaldehyde (1mmol) is reacted with guanidine hydrochloride (1mmol) and ethylacetoacetate (1mmol) as a catalyst in presence of p-toulene sulphonic acid monohydrate (PTSA) (1-3mmol %) in minimum amount of 1,4 dioxane is irradiated at 300W for 9-10(min). After the completion of reaction, product is poured into the cold water, filtered, washed with water, dried and is recrystallized using ethanol-acetic acid (2:1). This process yields the final product 1001 and yield is 90%

Example 2: Method of preparation of formula (II (a-i)) compounds (1002), (1003), (1004), (1005), (1006), (1007), (1008), (1009), (1010).
illustrated in Scheme-II

Conventional Method: Ethyl-2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)1,2,3,4-tetrahydropyrimidine-5-carboxylate (0.01 mol) (I) (1001) isrefluxed with various substituted aromatic aldehydes (0.01 mol) for 6 h in presence of catalytic amount of conc.HCl in 1,4 dioxane to affords 2-(substituted benzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihy-dropyrimidine-5-carboxylate II(a-i). Obtained product is poured into the cold water, filtered, washed with water and is recrystallized using acetic acid. This process yields the final products (1002), (1003), (1004), (1005), (1006), (1007), (1008), (1009), (1010).
Procedure B (under microwave-assisted solvent-free conditions):

Microwave Irradiation Method : Ethyl-2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)1,2,3, 4-tetrahydropyrimidine-5-carboxylate (1mmol) (I) (1001) is refluxed with various substituted aromatic aldehydes (1mmol) in presence of catalytic amount of conc. HCl and minimum amount of 1,4 dioxane is irradiated at 300 W for 10-12 min to affords 2-(substituted benzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihy-dropyrimidine-5-carboxylate II(a-i). Obtained product is poured into the cold water, filtered, washed with water, dried and was recrystallized using acetic acid. This process yields the final products (1002), (1003), (1004), (1005), (1006), (1007), (1008), (1009), (1010)
Example-3:

Spectral Data of (I)
Ethyl -2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5carboxylate (I) (1001)
FTIR (KBr, ? max , cm-1): 3455,3297,1729,1629
MS(m/z): 387.3(M+1)
1H NMR(400MHz,
DMSO-d6,d ppm): 8.4(br,1H,NH),8.1(br,1H,NH), 7.8(br,1H,NH),7.7-7.2(m,7H,ArH),
1.2(m,2H,OCH2),6.7(d,1H,CH),
3.4(s,3H,CH3),2.3(m,3H,ester CH3),
13C NMR(400MHz,
DMSO-d6,d ppm): 165.1,161.9,161.9,159.5,159.2,135.4,
128.9,127.8,124.8,124.0,122.6,122.3,
121.8,78.53,38.8,25.9,23.6.

Physicochemical Characterization of Ethyl -2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate (I) (1001) as reproduced below in table 1:
Table 1:
S.No m.p. (°C) Yield (%) Elemental composition Calculated (Observed)
Conventional MWI C H N
1 264 60 95 66.83
(65.79) 5.07
(5.00) 11.13
(11.10)

Example 4: Spectral data of formula(IIa-i)
(E)-ethyl-2-(4-methoxybenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(a) (1002)
FTIR (KBr, ? max , cm-1): 3327,1716,1622,1599
MS(m/z): 495.5(M+)
1H NMR(400MHz,
DMSO-d6,d ppm): 9.0(s,1H,NH),8.1-6.7(m,11H,ArH),
6.4(s,1H,HC=N),5.9(s,1H,CH), 4.3(m,3H,OCH3),3.9(s,3H,O-CH3),
2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )
13C NMR(400MHz,
DMSO-d6,d ppm): 165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86

(E)-ethyl-2-(3-nitrobenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(b) (1002)
FTIR (KBr, ? max , cm-1): 3327,1710,1632,1590

MS(m/z): 510.1(M+)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.2(s,1H,NH),8.5-6.7(m,11H,ArH),
6.4(s,1H,HC=N),6.0(s,1H,CH), 4.3(m,3H,OCH3),3.9(s,3H,O-CH3),
2.3(s,3H,CH 3 ), 1.5(m,2H,O-CH2 )

13C NMR(400MHz,
DMSO-d6,d ppm): 167.3,165.3,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,113.5,79.6,78.4,35.3

(E)-ethyl-2-(4-chlorobenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(c) (1004)
FTIR (KBr, ? max , cm-1): 3310,1706,1620,1600

MS(m/z): 499.1(M+)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.0(s,1H,NH),8.1-6.7(m,11H,ArH),
6.4(s,1H,HC=N),5.9(s,1H,CH), 4.3(m,3H,OCH3),3.9(s,3H,O-CH3),
2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )

13C NMR(400MHz,
DMSO-d6,d ppm): 165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86

(E)-ethyl-2-(2-chlorobenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(d) (1005)
FTIR (KBr, ? max , cm-1): 3310,1746,1640,1605

MS(m/z): 499.1(M+)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.3(s,1H,NH),8.1-6.7(m,11H,ArH),
6.4(s,1H,HC=N),5.9(s,1H,CH), 4.3(m,3H,OCH3),3.9(s,3H,O-CH3),
2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )

13C NMR(400MHz,
DMSO-d6,d ppm): 168.3,165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86

(E)-ethyl-4-methyl-2-(naphthalen-1-ylmethyleneamino)-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(e) (1010)

FTIR (KBr, ? max , cm-1): 3350,1700,1622,1609

MS(m/z): 515.1(M+1)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.6(s,1H,NH),8.6-6.7(m,14H,ArH),
6.4(s,1H,HC=N),5.9(s,1H,CH), 4.3(m,3H,OCH3),3.9(s,3H,O-CH3),
2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )

13C NMR(400MHz,
DMSO-d6,d ppm): 165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86

(E)-ethyl-2-(2-methoxybenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(f) (1009

FTIR (KBr, ? max , cm-1): 3327,1716,1622,1599

MS(m/z): 495.5(M+1)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.0(s,1H,NH),8.1-6.7(m,11H,ArH),
6.4(s,1H,HC=N),5.9(s,1H,CH), 4.3(m,3H,OCH3),3.9(s,3H,O-CH3),
2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )

13C NMR(400MHz,
DMSO-d6,d ppm): 165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86,15.32

(E)-ethyl-2-(4-(dimethylamino)benzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(g) (1006)

FTIR (KBr, ? max , cm-1): 3327,1716,1622,1599

MS(m/z): 508.2(M+)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.2(s,1H,NH),8.1-6.6(m,11H,ArH),
6.4(s,1H,HC=N),6.0(s,1H,CH), 4.3(t,3H,esterCH3),2.9(s,6H,N-(CH3)2),
2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )
13C NMR(400MHz,
DMSO-d6,d ppm): 168.4,167.2,165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86
(E)-ethyl-2-(4-fluorobenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(h) (1007)
FTIR (KBr, ? max , cm-1): 3256,1710,1620,1590

MS(m/z): 483.5(M+1)

1H NMR(400MHz,
DMSO-d6,d ppm): 9.2(s,1H,NH),8.1-6.5(m,11H,ArH),
6.4(s,1H,HC=N),5.5(s,1H,CH), 4.3(t,3H, ester CH3),2.5(s,3H,CH 3 ), 1.3(m,2H,O-CH2 )

13C NMR(400MHz,
DMSO-d6,d ppm): 168.4,167.2,165.1,161.9,159.4,159.2,135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86

(E)-ethyl-2-(4-hydroxy-3-methoxybenzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II(i) (1008)

FTIR (KBr, ? max , cm-1): 3317,3218,1726,1632,1579

MS(m/z): 511.5(M+1)

1H NMR(400MHz,
DMSO-d6,d ppm): 10.2(s,1H,OH),9.0(s,1H,NH),8.1-6.7(m,11H,ArH),6.4(s,1H,HC=N),5.9(s,1H,CH),4.3(m,3H,OCH3),3.9(s,3H,OCH3),2.5(s,3H,CH3),1.3(m,2H,O-CH2 )
13C NMR(400MHz,
DMSO-d6,d ppm): 165.1,161.9, 159.4,159.2, 153.5,
135.4,128.9,127.1,124.0,122.6,121.8,119.5,112.9,79.1,78.4,38.86

Physicochemical Characterization of Ethyl-2-(substituted benzylideneamino)-4-methyl-6-(4-oxo-4H-benzo[h]chromen-3-yl)-1,6-dihydropyrimidine-5-carboxylate II (a-i) as reproduced below in table 2:
Table 2

Compound
Ar
m.p. ° C
Yield (%) Elemental composition Calculated (Observed)
C H N
II(a) - 1002 C6H5-p-OCH3 192 62 70.29
(70.20) 5.09
(4.99) 8.48
(8.40)
II(b) -1003 C6H5-m- NO2 284 68 65.88 (65.38) 4.34 (4.20) 10.97 (10.35)
II(c) -1004 C6H5-p-Cl 170 64 67.27
(67.15) 4.44 (4.30) 8.40
(8.26)
II(d) -1005 C6H5-o- Cl 210 60 67.27
(67.30) 4.44 (4.35) 8.40
(8.16)
II(e) - 1010 C8H7 208 65 74.55 (74.39) 4.89 (4.76) 8.15
(7.99)
II(f) - 1009 C6H5-m-OCH3 180 60 70.29
(70.16) 5.09
(4.98) 8.48
(8.36)
II(g) - 1006 C8H10N 130 68 70.85 (70.21) 5.55 (5.82) 11.02 (10.89)
II(h) -1007 C6H5-p-F 140 50 69.56
(69.38) 4.59 (4.68) 8.69
(8.80)
II(i) -1008 C6H6O-m-OCH3 230 60 70.29
(69.95) 5.09 (4.92) 8.48 (8.34)

Example-5 In Vitro Anti-Cancer Analysis

EXPERIMENTAL PROCEDURE FOR SRB ASSAY
The cell lines are grown in RPMI 1640 medium containing 10% fetal bovine serum and 2 mM L-glutamine. For present screening experiment, cells are inoculated into 96 well microlitre plates in 100 µL at plating densities as shown in the study details above, depending on the doubling time of individual cell lines. After cell inoculation, the microlitre plates are incubated at 37° C, 5 % CO2, 95 % air and 100 % relative humidity for 24 h prior to addition of experimental drugs.
After 24 h, one 96 well plate containing 5*103cells/well is fixed in situ with TCA, to represent a measurement of the cell population at the time of drug addition (Tz). Experimental drugs are initially solubilized in dimethyl sulfoxide at 100mg/ml and diluted to 1mg/ml using water and stored frozen prior to use. At the time of drug addition, an aliquote of frozen concentrate (1mg/ml) is thawed and diluted to 100 µg/ml, 200 µg/ml, 400 µg/ml and 800 µg/ml with complete medium containing test article. Aliquots of 10 µl of these different drug dilutions are added to the appropriate microlitre wells already containing 90 µl of medium, resulting in the required final drug concentrations i.e.10 µg/ml, 20 µg/ml, 40 µg/ml, 80 µg/ml.

ENDPOINT MEASUREMENT

After compound addition, plates are incubated at standard conditions for 48 hours and assay is terminated by the addition of cold TCA. Cells are fixed in situ by the gentle addition of 50 µl of cold 30 % (w/v) TCA (final concentration, 10 % TCA) and incubated for 60 minutes at 4°C. The supernatant is discarded; the plates are washed five times with tap water and air dried. Sulforhodamine B (SRB) solution (50 µl) at 0.4 % (w/v) in 1 % acetic acid is added to each of the wells, and plates are incubated for 20 minutes at room temperature. After staining, unbound dye is recovered and the residual dye is removed by washing five times with 1 % acetic acid. The plates are air dried. Bound stain issubsequently eluted with 10 mM trizma base, and the absorbance is read on an plate reader at a wavelength of 540 nm with 690 nm reference wavelength.
Percent growth iscalculated on a plate-by-plate basis for test wells relative to control wells. Percent Growth is expressed as the ratio of average absorbance of the test well to the average absorbance of the control wells * 100.
Using the six absorbance measurements [time zero (Tz), control growth (C), and test growth in the presence of drug at the four concentration levels (Ti)], the percentage growth is calculated at each of the drug concentration levels. Percentage growth inhibition is calculated as:
[(Ti-Tz)/(C-Tz)] x 100 for concentrations for which Ti>/=Tz (Ti-Tz) positive or zero [(Ti-Tz)/Tz] x 100 for concentrations for which Ti80 >80 <10
2 II1002 >80 >80 <10
3 IIb - 1003 >80 72.2 <10
4 Iic - 1004 >80 53.7 <10
5 Iid -1005 >80 >80 <10
7 Iie -1010 >80 >80 <10
8 Iif - 1009 >80 >80 <10
9 Iig -1006 >80 >80 <10
10 Iih -1007 >80 >80 <10
11 Iii -1008 >80 >80 <10
12 Adriamycin(Doxorubicin) 56.0 16.9 <10

From the Table 3 it is found that all the synthesized compounds shows good anticancer activity against HeLa Cell line.
,CLAIMS: We claim:
1. A novel dihydropyrimidine compound of Formula-I and derivatives, intermediates thereof.

wherein each substituent is selected independently
R1 is

R1’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’ is --H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R6’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

is single bond, double bond;
R2 is

,
wherein each substituent is selected independently
R1’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’’is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

R3 is –CH3, -C2H5, –O-CH3, -O-C2H5

R4 is ,
R1’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4 is substituted naphthalene ring
R1’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R2’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R3’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R4’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R5’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R6’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
R7’’’’ is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

R4 is substituted naphthalene ring
Ra is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rb is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rc is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rd is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Re is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rf is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH
Rg is -H, -Cl, -Br, -I, F, -NO2, -N-(CH3)2, -O-CH3, -O-C2H5, -CH3, -C2H5, -OTs, -CN, OH

2. The compounds as claimed in claim 1, wherein the compound is
1. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
2. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
3. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
4. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
5. ethyl 2-imino-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
6. (E)-ethyl 2-((4-(dimethylamino)benzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
7. (E)-ethyl 2-((4-fluorobenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
8.(E)-ethyl-2-((4-hydroxy-2-methoxybenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
9. (E)-ethyl 2-((2-methoxybenzylidene)amino)-6-methyl-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate;
10. (E)-ethyl 6-methyl-2-((naphthalen-1-ylmethylene)amino)-4-(4-oxo-4H-benzo[h]chromen-3-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

3. A process for the preparation of compound of formula (I) and intermediates, derivatives
thereof as claimed in claim 1
comprising the steps of:
i) refluxing or microwave irradiation of the compound (100), compound (200) and guanidine hydrochloride in presence of a solvent and catalyst to obtain compound (300) of formula - I

ii) – refluxing the compound (300) with compound (400) in presence of an acid and a solvent to obtain compound (500) of formula - I

Scheme-II
4. The process as claimed in claim 1, wherein the the catalyst used in step (i) is selected from the group comprising p-toulene sulphonic acid monohydrate (PTSA).
5. The process as claimed in claim 1, wherein the solvent used in step (i) and step(ii) is selected from the group comprising 1,4 Dioxane.
6. The compounds as claimed in claim 1, wherein the formula I comprises its pharmaceutically acceptable salts, hydrates, solvates, crystal forms salts, stereoisomers and individual diastereomers thereof, individual diastereomers, pharmaceutically acceptable carrier thereof.

7. Use of the compound of formula 1 as claimed in claim 1 as anticancer agent.