854
A. K. Chakraborti et al.
LETTER
(d, J = 7.9 Hz, 1 H), 7.98 (d, J = 8.1 Hz, 1 H). 13C NMR (300 MHz,
CDCl3): d = 40.46, 55.02, 113.24, 115.28, 121.92, 121.97, 123.20,
125.28, 126.41, 130.33, 136.13, 139.08, 153.67, 160.38, 171.46.
MS (EI): m/z = 255 (M+), 240 (M+ – CH3), 224 (M+ – OCH3), 91
(C7H7 ), 77 (C6H5 ). Anal. Calcd for C15H13NOS: C, 70.56; H, 5.13;
N, 5.49; S, 12.56. Found: C, 70.61; H, 5.19; N, 5.53; S, 12.51.
References
(1) (a) Hall, I. H.; Peaty, N. J.; Henry, J. R.; Easmon, J.;
Heinisch, G.; Purstinger, G. Arch. Pharm. 1999, 332, 115.
(b) Bénéteau, V.; Besson, T.; Guillard, J.; Léonce, S.;
Pfeiffer, B. Eur. J. Med. Chem. 1999, 34, 1053.
(c) Hutchinson, I.; Bradshaw, T. D.; Matthews-Stevens, M.
F. G.; Westwell, A. D. Bioorg. Med. Chem. Lett. 2003, 13,
471; and the references therein.
+
+
2-(Phenoxymethyl)benzothiazole (entry 10 in Table 2): mp 86 °C.
IR (KBr): 3052, 2902, 1593, 1523, 1492, 1436, 1255 cm–1. 1H NMR
(300 MHz, CDCl3): d = 5.50 (s, 2 H), 6.99–7.06 (m, 3 H), 7.29–7.35
(m, 2 H), 7.38–7.43 (m, 1 H), 7.48–7.53 (m, 1 H), 7.90 (d, J = 8.0
Hz, 1 H), 8.04 (d, J = 8.1 Hz, 1 H). MS (EI): m/z = 241 (M+), 164
(2) Palmer, P. J.; Trigg, R. B.; Warrington, J. V. J. Med. Chem.
1971, 14, 248.
(3) (a) Benazzouz, A.; Boraud, T.; Dubédat, P.; Boireau, A.;
Stutzmann, J.-M.; Gross, C. Eur. J. Pharmacol. 1995, 284,
299. (b) Jimonet, P.; Audiau, F.; Barreau, M.; Blanchard,
J.-C.; Boireau, A.; Bour, Y.; Coléno, M.-A.; Doble, A.;
Doerflinger, G.; Huu, C. D.; Donat, M.-H.; Duchesne, J. M.;
Ganil, P.; Guérémy, C.; Honoré, E.; Just, B.; Kerphirique,
R.; Gontier, S.; Hubert, P.; Laduron, P. M.; Blevec, J. L.;
Meunier, M.; Miquet, J.-M.; Nemecek, C.; Pasquet, M.; Piot,
O.; Pratt, J.; Rataud, J.; Reibaud, M.; Stutzmann, J.-M.;
Mignani, S. J. Med. Chem. 1999, 42, 2828.
(4) Lara, B.; Gandia, L.; Tores, A.; Martinez-Sierra, R.; Garcia,
A. G.; Lopez, M. G. Eur. J. Pharmacol. 1997, 325, 109.
(5) (a) Mylari, B. L.; Larson, E. R.; Beyer, T. A.; Zembrowski,
W. J.; Aldinger, C. E.; Dee, M. F.; Siegel, T. W.; Singleton,
D. H. J. Med. Chem. 1991, 34, 108. (b) Kotani, T.; Nagaki,
Y.; Ishii, A.; Konishi, Y.; Yago, H.; Suehiro, S.; Okukado,
N.; Okamoto, K. J. Med. Chem. 1997, 40, 684.
(6) (a) Sato, G.; Chimoto, T.; Aoki, T.; Hosokawa, S.;
Sumigama, S.; Tsukidate, K.; Sagami, F. J. Toxicol. Sci.
1999, 24, 165. (b) Naitoh, T.; Kawaguchi, S.; Kakiki, M.;
Ohe, H.; Kajiwara, A.; Horie, T. Xenobiotica 1998, 28, 269.
(c) Kagaya, T.; Kajiwara, A.; Nagato, S.; Akasaka, K.;
Kubota, A. J. Pharmacol. Exp. Ther. 1996, 278, 243.
(7) (a) Hadjipavlou-Litina, D. J.; Geronikaki, A. A. Drug Des.
Discovery 1997, 15, 199. (b) Oketani, K.; Inoue, T.;
Murakami, M. Eur. J. Pharmacol. 2001, 427, 159.
(8) Paramashivappa, R.; Phani Kumar, P.; Subba Rao, P. V.;
Srinivasa Rao, A. Bioorg. Med. Chem. Lett. 2003, 13, 657.
(9) Nagel, A. A.; Liston, D. R.; Jung, S.; Mahar, M.; Vincent, L.
A.; Chapin, D.; Chen, Y. L.; Hubbard, S.; Ives, J. L.; Jones,
S. B. J. Med. Chem. 1995, 38, 1084.
(M+ – C6H5), 148 (M+ – C6H5O), 77 (C6H5 ). Anal. Calcd for
+
C14H11NOS: C, 69.68; H, 4.59; N, 5.80; S, 13.29. Found: C, 69.63;
H, 4.62; N, 5.76; S, 13.31.
2-(Thiophenoxymethyl)benzothiazole (entry 11 in Table 2): mp
44 °C. IR (KBr): 3057, 2997, 1582, 1508, 1479, 1434, 1312, 1245,
1
1094, 1063 cm–1. H NMR (300 MHz, CDCl3): d = 4.49 (s, 2 H),
7.13–7.34 (m, 4 H), 7.37–7.46 (m, 3 H), 7.77 (d, J = 7.8 Hz, 1 H),
7.94 (d, J = 8.2 Hz, 1 H). 13C NMR (300 MHz, CDCl3): d = 36.81,
121.65, 122.90, 125.11, 126.05, 127.01, 129.13, 129.78, 134.51,
135.69, 153.11, 169.94. MS (EI): m/z = 257 (M+), 148 (M+
C6H5S), 77 (C6H5 ). Anal. Calcd for C15H13NS: C, 65.33; H, 4.31;
N, 5.44; S, 24.92. Found: C, 65.42; H, 4.37; N, 5.49; S, 24.83.
–
+
2-(1-Naphthylmethyl)benzothiazole (entry 17 in Table 2): mp
103 °C. IR (KBr): 3055, 2900, 1922, 1805, 1591, 1554, 1509, 1432,
1
1244 cm–1. H NMR (300 MHz, CDCl3): d = 4.84 (s, 2 H), 7.19–
7.24 (m, 1 H), 7.37–7.51 (m, 5 H), 7.64 (d, J = 7.9 Hz, 1 H), 7.79–
7.84 (m, 2 H), 8.01 (d, J = 8.1 Hz, 1 H), 8.05–8.08 (m, 1 H). 13C
NMR (300 MHz, CDCl3): d = 38.36, 121.42, 122.64, 123.88,
124.66, 125.49, 125.83, 125.87, 126.48, 127.79, 128.45, 128.72,
131.79, 133.20, 133.93, 135.56, 153.09, 171.77. MS (EI): m/z = 275
(M+). Anal. Calcd for C18H13NS: C, 78.51; H, 4.76; N, 5.09; S,
11.64. Found: C, 79.13; H, 5.03; N, 5.67; S, 11.47.
2-(1-Cycloheptyl)benzothiazole (entry 18 in Table 2): IR (KBr):
1
2926, 2854, 1609, 1512, 1458, 1440, 1274 cm–1. H NMR (300
MHz, CDCl3): d = 1.50–1.70 (m, 6 H), 1.70–2.00 (m, 4 H), 2.10–
2.30 (m, 2 H), 3.20–3.35 (m, 1 H), 7.30–7.36 (m, 1 H), 7.41–7.46
(m, 1 H), 7.84 (d, J = 7.9 Hz, 1 H), 7.97 (d, J = 8.1 Hz, 1 H). 13C
NMR (300 MHz, CDCl3): d = 26.51, 28.04, 35.35, 45.48, 121.51,
122.48, 124.50, 125.80, 134.62, 152.92, 178.83. MS (EI): m/z = 231
(M+). Anal. Calcd for C14H17NS: C, 72.68; H, 7.41; N, 6.05; S,
13.86. Found: C, 72.54; H, 7.48; N, 6.11; S, 13.82.
(10) Matthews, J. H.; Krishnan, R.; Costanzo, M. J.; Maryanoff,
B. E.; Tulinsky, A. Biophys. J. 1996, 2830.
(11) Caccese, R. G.; DiJoseph, J. F.; Scotnicki, J. S.; Borella, L.
E.; Adams, L. M. Agents Actions 1991, 34, 223.
(12) Sohn, S. K.; Chang, M. S.; Choi, W. S.; Kim, K. B.; Woo, T.
W.; Lee, S. B.; Chung, Y. K. Can. J. Physiol. Pharmacol.
1999, 77, 330.
(13) Surgue, M. F.; Gautheron, P.; Schmitt, C.; Viader, M. P.;
Conquet, P.; Smith, R. L.; Share, N. N.; Stone, C. A. J.
Pharmacol. Exp. Ther. 1985, 232, 534.
1,2-Bis(2-Benzothiazolyl)benzene (4): mp 94 °C. IR (KBr): 3358,
1
3055, 2915, 1594, 1433, 1314, 1222, 1017 cm–1. H NMR (300
MHz, CDCl3): d = 7.35–7.40 (m, 2 H), 7.46–7.51 (m, 2 H), 7.64
(dd, J = 5.7 Hz, 3.3 Hz, 2 H), 7.81 (d, J = 7.9 Hz, 2 H), 7.95 (dd,
J = 5.7 Hz, 3.3 Hz, 2 H), 8.05 (d, J = 8.3 Hz, 2 H). 13C NMR (300
MHz, CDCl3): d = 121.52, 123.73, 125.36, 126.23, 130.31, 130.98,
133.56, 136.64, 153.21, 166.19. MS (APCI): m/z = 345.3 (M+ +1).
Anal. Calcd for C20H12N2S2: C, 69.74; H, 3.51; N, 8.13; S, 18.62.
Found: C, 69.78; H, 3.54; N, 8.10; S, 18.58.
(14) Phoon, C. W.; Ng, P. Y.; Ting, A. E.; Yeo, S. L.; Sim, M. M.
Bioorg. Med. Chem. Lett. 2001, 11, 1647.
1,2-Bis(2-benzothiazolyl)ethane (6): mp 137 °C. IR (KBr): 3055,
2310, 1904, 1782, 1591, 1510, 1454, 1440, 1319, 1212, 1090, 1061
cm–1. 1H NMR (300 MHz, CDCl3): d = 3.73 (s, 4 H), 7.32–7.37 (m,
2 H), 7.43–7.48 (m, 2 H), 7.81 (d, J = 7.9 Hz, 2 H), 7.99 (d, J = 8.1
Hz, 2 H). 13C NMR (300 MHz, CDCl3): d = 33.21, 121.54, 122.71,
124.94, 126.03, 135.19, 153.12, 169.18. MS (APCI) m/z = 297.0
(M+ +1). Anal. Calcd for C16H12N2S2: C, 64.83; H, 4.08; N, 9.45; S,
21.64. Found: C, 64.86; H, 4.10; N, 9.41; S, 21.63.
(15) Loos, D.; Sidoova, E.; Sutoris, V. Molecules 1999, 4, 81; and
the references cited therein.
(16) Ivanov, S. K.; Yuritsyn, V. S. Neftekhimiya 1971, 11, 99;
Chem. Abstr. 1971, 74, 124487m.
(17) Monsanto Co. Brit. Pat. 1,106,577, 1968; Chem. Abstr.
1968, 68, 96660t.
(18) Kashiyama, E.; Hutchinson, I.; Chua, M. S.; Stinson, S. F.;
Phillips, L. R.; Kaur, G.; Sausville, E. A.; Bradshaw, T. D.;
Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 1999, 42,
4172.
(19) Boger, D. E. J. Org. Chem. 1978, 43, 2296.
(20) Cohen, V. I.; Pourabass, S. J. Heterocycl. Chem. 1977, 14,
1321.
(21) Cohen, V. I. J. Heterocycl. Chem. 1979, 16, 13.
Synlett 2004, No. 5, 851–855 © Thieme Stuttgart · New York