Antiprotozoal quinones. IV. 2-Amino-1,4-naphthoquinone imines as potential antimalarials

Journal of Medicinal Chonistry, 1.970, T'ol. 12, S o . 3 551

NOTES

II

N-Rl Yield

R'

No. 3 4

5 6 7

a 9 10 11

12

CHI (CHdnCHa (CH?)3C H3 ( C HdsC Ha (CHdioCHs (CHz)iiCH3 (CHdiaCH3 CH(CH~~(CHP)SCH(CHS)J

0 0

hIp, CHI ( CH d ?CHI (CHI)3C H3 (CHdsCHa (CH~IOCHI (CH~IICHP (CHdiaCH3 CH(CH3j(CH2)3CH(CH3)a

0 0

13

o c

132-133 dec 114-115 dec 93-93,s 64-64.5

53.5-54.5 52,543 53-53.5 55-56

22 41 24 24 24 22

27 13

116-1 17

31

175-176

19

75-76

39

116.5-1 17

14

(56)

18

18

85-86

30

16

77-78

22

17

73-i4

21

18

83-84

24

19

61-62

33

20

6T-68

24

CaHisNnOi

21

88.5-89

as

CaH?sN?O

22

103.5-104.5

54

23

(CHz)sCH3

80-81

36

24

(CHJ)SCHI

74.5-i5

67

25

(CHdsCHa

54-55

80

123-124

63

27

103.5-104.5

46

28 29 30

a2,5-83

40 27 49

31

103-103.5

64

32

106.5-10i.5

78

26

a

C6HS

85.5-86.5 82 5 - 8 3 . 5

CPOHMN?O

C : Calcd, 79.48; Found, 79.04.

been obtained iriciderital to other chemical studies,2 while activity against Mycobacterium tuberculosis in mice has been claimed for a few other^.^ The structural (2) Cf. T. Zincke a n d E. Kiegel, Ber.. 81, 1039 (1888); L. F. Fieser and C. I