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Table 1 Synthesized DHPM derivatives

From: Impact of kinesin Eg5 inhibition by 3,4-dihydropyrimidin-2(1H)-one derivatives on various breast cancer cell features

Ent

Reagent

Prod.

Yield (%)

R1

R2

R3

X

1

Ph

Me

Me

O

4c

99

2

Ph

OCH2CH3

Me

S

4d

93

3

Ph

Me

Me

S

4e

83

4

4-Cl-Ph

OCH2CH3

Me

O

4f

87

5

4-Cl-Ph

OCH2CH3

Me

S

4h

80

6

4-Cl-Ph

Me

Me

S

4i

77

7

3-OH-Ph

OCH2CH3

Me

O

4j

98

8

3-OH-Ph

Me

Me

O

4k

80

9a

3-OH-Ph

OCH2CH3

Me

S

Mon

93

10

3-OH-Ph

Me

Me

S

4m

88

11

2-OH-Ph

OCH2CH3

Me

O

4n

84

12

2-OH-Ph

Me

Me

O

4o

80

13

2-OH-Ph

OCH2CH3

Me

S

4p

84

14

2-OH-Ph

Me

Me

S

4q

90

15

3-NO2-Ph

OCH2CH3

Me

O

4r

96

16

3-NO2-Ph

OCH2CH3

Me

S

4t

86

17

3-NO2-Ph

Me

Me

S

4u

86

18

2-NO2-Ph

OCH2CH3

Me

O

4v

70

19

2-NO2-Ph

Me

Me

O

4x

60

20

2-NO2-Ph

Me

Me

S

4z

60e

21

4-OH-3-MeO-Ph

OCH2CH3

Me

O

4ba

98

22

4-OH-3-MeO-Ph

OCH2CH3

Me

S

4bc

85

23

4-OH-3-MeO-Ph

Me

Me

S

4bd

85

24

H

OCH2CH3

Me

O

4be

96

25

Me

Me

Me

O

4bj

66

26

Me

OCH2CH3

Me

S

4bk

70

27

OCH2CH3

Me

O

4bm

87

28

Me

Me

O

4bn

79

29b

OCH2CH3

Me

S

4bo

70

30

Me

Me

S

4bp

71

31

3-OH-Ph

O

4bq

60

32c

3-OH-Ph

S

4br

72

33

3-OH-Ph

O

4bs

70

34d

3-OH-Ph

S

4bt

70

35

OCH2CH3

Me

O

4bu

66f

36

Me

Me

S

4bv

50f

37

OCH2CH3

Me

S

4bx

42f

38

Me

Me

O

4by

83

  1. aMonastrol. bPiperastrol. cEnastron. dDimethylenastron. e12 h of reaction. fProduct formation was above 90%, but there was considerable loss during purification column chromatography.
  2. 37 DHPM derivatives and monastrol were studied in this work.