Biological Activities of 3-(5-Oxazolyl)indole Natural Products and Advances on Synthesis of Its Derivatives
- Corresponding author: Zhang Mingzhi, mzzhang@njau.edu.cn Zhang Weihua, zhwh@njau.edu.cn
Citation:
Shi Zhan, Nie Kerui, Liu Chang, Zhang Mingzhi, Zhang Weihua. Biological Activities of 3-(5-Oxazolyl)indole Natural Products and Advances on Synthesis of Its Derivatives[J]. Chinese Journal of Organic Chemistry,
;2020, 40(2): 327-338.
doi:
10.6023/cjoc201907047
Zhang, M. Z.; Chen, Q.; Yang, G. F. Eur. J. Med. Chem. 2015, 89, 421.
doi: 10.1016/j.ejmech.2014.10.065
Li, Q. X.; Shi, X. F.; Huang, Z.; Tian, X. P.; Wang, F. Z. J. Trop. Oceanogr. 2013, (1), 35 (in Chinese).
doi: 10.3969/j.issn.1009-5470.2013.01.005
Bhate, D. S.; Hulyalkar, R. K.; Menon, S. K. Experientiu 1960, 16, 504.
doi: 10.1007/BF02158365
Bhate, D. S.; Ambekar, G. R.; Bhatnagar, K. K.; K., H. R. Hind. Antibiot. Bull. 1961, 4, 139.
Joshi, B. S.; Taylor, W. I.; Bhate, D. S.; Karmarkar, S. S. Tetrahedron 1963, 19, 1437.
doi: 10.1016/S0040-4020(01)98569-2
Koyama, Y.; Yokose, K.; Dolby, L. J. Agric. Biol. Chem. 1981, 45, 1285.
Naik, S. R.; Harindran, J.; Varde, A. B. J. Biotechnol. 2001, 88, 1.
doi: 10.1016/S0168-1656(01)00244-9
Roy, S.; Haque, S.; Gribble, G. W. Synthesis 2006, 3948.
Khan, S.; Ahmed, M. S.; Arakawa, O.; Onoue, Y. J. J. Aquacult. Bamidgeh. 1995, 47, 137.
Khan, S.; Arakawa, O.; Onoue, Y. Phycologia 1996, 35, 239.
doi: 10.2216/i0031-8884-35-3-239.1
Pettit, G. R.; Knight, J. C.; Herald, D. L.; Davenport, R.; Pettit, R. K.; Tucker, B. E.; Schmidt, J. M. J. Nat. Prod 2002, 65, 1793.
doi: 10.1021/np020173x
Miao, Y. P.; Wen, R.; Hitoshi, A.; Zhou, P. G. Acta Pharm. Sinica 2004, 39, 37.
Watanabe, H.; Amano, S.; Yoshida, J.; Takase, Y.; Miyadoh, S.; Sasaki, T.; Hatsu, M.; Takeuchi, Y.; Komada, Y. Meiji Seika Kenkyu Nenpo 1988, 27, 55.
Shin, H. J.; Jeong, H. S.; Lee, H. S.; Park, S. K.; Kim, H. M.; Kwon, H. J. J. Microbiol. Biotechnol. 2007, 17, 1403.
Romero, F. A.; Du, W.; Hwang, I.; Rayl, T. J.; Kimball, F. S.; Leung, D.; Hoover, H. S.; Apodaca, R. L.; Breitenbucher, J. G.; Cravatt, B. F.; Boger, D. L. J. Med. Chem. 2007, 50, 1058.
doi: 10.1021/jm0611509
Shin, D. Y.; Shin, H. J.; Kim, G. Y.; Cheong, J.; Choi, I. W.; Kim, S. K.; Moon, S. K.; Kang, H. S.; Choi, Y. H. J. Microbiol. Biotechnol. 2008, 18, 1862.
Shim, D. W.; Shin, H. J.; Han, J. W.; Ji, Y. E.; Jang, C. H.; Koppula, S.; Kang, T. B.; Lee, K. H. Toxicol. Appl. Pharm. 2015, 284, 227.
doi: 10.1016/j.taap.2015.02.006
Takahashi, S.; Matsunaga, T.; Hasegawa, C.; Saito, H.; Fujita, D.; Kiuchi, F.; Tsuda, Y. Chem. Pharm. Bull. 1998, 46, 1527.
doi: 10.1248/cpb.46.1527
Davies, J. R.; Kane, P. D.; Moody, C. J.; Slawin, A. M. Z. J. Org. Chem. 2005, 70, 5840.
doi: 10.1021/jo050303h
Miao, Y. P. Ph.D. Dissertation, Fudan University, Shanghai, 2003 (in Chinese).
Diaye, N.; Guella, G.; Mancini, I.; Pietra, F. Tetrahedron Lett. 1996, 37, 3049.
doi: 10.1016/0040-4039(96)00466-2
Lindquist, N.; Fenical, W.; Vanduyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303.
doi: 10.1021/ja00006a060
Nicolaou, K. C.; Chen, D. Y.; Huang, X.; Ling, T.; Bella, M.; Snyder, S. A. J. Am. Chem. Soc. 2004, 126, 12888.
doi: 10.1021/ja040092i
Somei, M.; Sato, H.; Komura, N.; Kaneko, C. Heterocycles 1985, 23, 1101.
doi: 10.3987/R-1985-05-1101
Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223.
doi: 10.1016/S0040-4039(98)00231-7
Wipf, P.; Methot, J. L. Org. Lett. 2001, 3, 1261.
doi: 10.1021/ol0157196
Bagley, M. C.; Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897.
doi: 10.1016/S0040-4039(00)01120-5
Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627.
doi: 10.1016/S0040-4039(00)02023-2
Roy, S.; Eastman, A.; Gribble, G. W. Org. Biomol. Chem. 2006, 4, 3228.
doi: 10.1039/b607504e
Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
doi: 10.1021/jo00066a004
Bergman, J.; Backvall, J. E.; Lindstrom, J. O. Tetrahedron 1973, 29, 971.
doi: 10.1016/0040-4020(73)80047-X
Deng, W. P.; Nam, G.; Fan, J. F.; Kirk, K. L. J. Org. Chem. 2003, 68, 2798.
doi: 10.1021/jo020731c
Jiang, B.; Gu, X. H. Bioorgan. Med. Chem. 2000, 8, 363.
doi: 10.1016/S0968-0896(99)00290-4
Fresneda, P. M.; Molina, P.; Sanz, M. A. Synlett 2001, 218.
Radspieler, A. Ph.D. Dissertation, Humboldt University, Berlin, 2000.
Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1977, 42, 1213.
doi: 10.1021/jo00427a024
Kumar, D.; Sundaree, S.; Patel, G.; Rao, V. S. Tetrahedron Lett 2008, 49, 867.
doi: 10.1016/j.tetlet.2007.11.173
Koser, G. F.; Relenyi, A. G.; Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47, 2487.
doi: 10.1021/jo00133a053
oser, G. F. Adv. Heterocycl. Chem. 2004, 86, 225.
doi: 10.1016/S0065-2725(03)86004-X
Kelly, T. R.; Fu, Y.; Xie, R. L. Tetrahedron Lett. 1999, 40, 1857.
doi: 10.1016/S0040-4039(99)00074-X
Doyle, K. J.; Moody, C. J. Synthesis 1994, 1021.
Brain, C. T.; Paul, J. M. Synlett 1999, 1642.
Nishida, A.; Fuwa, M.; Naruto, S.; Sugano, Y.; Saito, H.; Nakagawa, M. Tetrahedron Lett. 2000, 41, 4791.
doi: 10.1016/S0040-4039(00)00677-8
Liu, S. F.; Wu, Q. G.; Schmider, H. L.; Aziz, H.; Hu, N. X.; Popovic, Z.; Wang, S. N. J. Am. Chem. Soc. 2000, 122, 3671.
doi: 10.1021/ja9944249
Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451.
doi: 10.1021/jo00350a001
Miyake, F.; Hashimoto, M.; Tonsiengsom, S.; Yakushijin, K.; Horne, D. A. Tetrahedron 2010, 66, 4888.
doi: 10.1016/j.tet.2010.03.109
Lade, D. M.; Krishna, V. S.; Sriram, D.; Rode, H. B. Chemistryselect 2017, 2, 1250.
doi: 10.1002/slct.201601821
Dhar, T. G. M.; Shen, Z. Q.; Fleener, C. A.; Rouleau, K. A.; Barrish, J. C.; Hollenbaugh, D. L.; Iwanowicz, E. J. Bioorg. Med. Chem. Lett. 2002, 12, 3305.
doi: 10.1016/S0960-894X(02)00748-5
Van Leusen, D.; Hessen, B. Organometallics 2001, 20, 224.
doi: 10.1021/om000678n
Houwing, H. A.; Wildeman, J.; Van Leusen, A. M. J. Heterocycl. Chem. 1981, 18, 1133.
doi: 10.1002/jhet.5570180615
Chakrabarty, M.; Basak, R.; Harigaya, Y.; Takayanagi, H. Tetrahedron 2005, 61, 1793.
doi: 10.1016/j.tet.2004.12.022
Zhang, M. Z.; Chen, Q.; Mulholland, N.; Beattie, D.; Irwin, D.; Gu, Y. C.; Yang, G. F.; Clough, J. Eur. J. Med. Chem. 2012, 53, 283.
doi: 10.1016/j.ejmech.2012.04.012
Boto, A.; Ling, M.; Meek, G.; Pattenden, G. Tetrahedron Lett. 1998, 39, 8167.
doi: 10.1016/S0040-4039(98)01819-X
Barrett, G. M.; Kohrt, J. T. Synlett 1995, 415.
Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis 1987, 693.
Kelly, T. R.; Lang, F. R. J. Org. Chem. 1996, 61, 4623.
doi: 10.1021/jo960433d
Primas, N.; Bouillon, A.; Lancelot, J. C.; Rault, S. Tetrahedron 2009, 65, 6348.
doi: 10.1016/j.tet.2009.06.023
Besselievre, F.; Mahuteau-Betzer, F.; Grierson, D. S.; Piguel, S. J. Org. Chem. 2008, 73, 3278.
doi: 10.1021/jo7027135
Ohnmacht, S. A.; Mamone, P.; Culshaw, A. J.; Greaney, M. F. Chem Commun 2008, 1241.
Do, H. Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
doi: 10.1021/ja075802+
Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 1970.
doi: 10.1016/j.tet.2006.12.068
Bellina, F.; Cauteruccio, S.; Rossi, R. Eur. J. Org. Chem. 2006, 1379.
Del Zotto, A.; Amoroso, F.; Baratta, W.; Rigo, P. Eur. J. Org. Chem. 2009, 110.
Liu, W. J.; Xie, Y. X.; Yun, L. A.; Li, J. H. Synthesis 2006, 860.
Alimardanov, A.; de Vondervoort, L. S. V.; de Vries, A. H. M.; de Vries, J. G. Adv. Synth. Catal. 2004, 346, 1812.
doi: 10.1002/adsc.200404210
Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973.
doi: 10.1021/ol0263907
Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390.
doi: 10.1021/jm9800853
Lancelot, J. C.; Prunier, H.; Robba, M.; Delagrange, P.; Renard, P.; Adam, G. EP623620 A1, 1994.
Zhang, F. Z.; Greaney, M. F. Org. Lett. 2010, 12, 4745.
doi: 10.1021/ol1019597
Wu, Y. D.; Peng S.; Ou-yang, Y. J.; Qian, P. C.; He, W. M.; Xiang, J. N. Acta Chim. Sinica 2012, 70, 47 (in Chinese).
Zhou, H. P.; Gai, K.; Lin, A. J.; Xu, J. Y.; Wu, X. M.; Yao, H. Q. Org. Biomol. Chem. 2015, 13, 1.
doi: 10.1039/C5OB90001H
(a) Zhu, Y. P.; Fei, Z.; Liu, M. C.; Jia, F. C.; Wu, A. X. Org. Lett. 2013, 15, 378.
(b) Xiang, J. C.; Wang, J. G.; Wang, M.; Meng, X. G.; Wu, A. X. Tetrahedron 2014, 70, 7470.
Liu, B.; Li, R.; Li, Y. A.; Li, S. Y.; Yu, J.; Zhao, B. F.; Liao, A. C.; Wang, Y.; Wang, Z. W.; Lu, A. D.; Liu, Y. X.; Wang, Q. M. J. Agric. Food Chem. 2019, 67, 1795.
doi: 10.1021/acs.jafc.8b06175
Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959.
doi: 10.1021/jo00293a053
Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609.
Vedejs, E.; Barda, D. A. Org. Lett. 2000, 2, 1033.
doi: 10.1021/ol005548p
Schöllkopf, U.; Schröder, R. Angew. Chem., Int. Ed. 1971, 10, 333.
doi: 10.1002/anie.197103331
Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214.
doi: 10.15227/orgsyn.063.0214
Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158.
doi: 10.1021/jo962169u
Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
Adreani, A.; Bonazzi, D.; Rambaldi, M.; Guarnieri, A. J. Med. Chem. 1977, 20, 1344.
doi: 10.1021/jm00220a023
Olah, G. A.; Arranaghi, M.; Prakash, G. K. Synthesis 1983, 8, 636.
Yang, C. J.; Chen, X. Y.; Tang, T.; He, Z. J. Org. Lett. 2016, 18, 1486
doi: 10.1021/acs.orglett.6b00456
Liu, X. Z.; Zhou, Y. X.; Chen, G. J.; Yang, Z. Q.; Li, Q.; Liu, P. J. Org. Biomol. Chem. 2018, 16, 3572.
doi: 10.1039/C8OB00833G
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