综述与进展

一氧化氮供体化合物的合成方法研究进展

  • 王兵 ,
  • 李娜 ,
  • 刘腾 ,
  • 王英爱 ,
  • 王晓静 ,
  • 孙捷
展开
  • a. 济南大学 山东省医学科学院 医学与生命科学学院 济南 250200;
    b. 山东省医学科学院药物研究所 国家卫生部生物技术药物重点实验室 山东省罕少见病重点实验室 济南 250062

收稿日期: 2016-10-21

  修回日期: 2016-12-29

  网络出版日期: 2017-01-20

基金资助

山东省自然科学基金(No.ZR2015YL041)资助项目.

Research Progress on Synthesis of Nitric Oxide Donor Compounds

  • Wang Bing ,
  • Li Na ,
  • Liu Teng ,
  • Wang Ying'ai ,
  • Wang Xiaojing ,
  • Sun Jie
Expand
  • a. School of Medicine and Life Sciences, University of Jinan-Shandong Academy of Medical Sciences, Jinan 250200;
    b. Key Laboratory for Biotech-Drugs Ministry of Health, Key Laboratory for Rare & Uncommon Diseases of Shandong Province, Institute of Materia Medica, Shandong Academy of Medical Sciences, Jinan 250062

Received date: 2016-10-21

  Revised date: 2016-12-29

  Online published: 2017-01-20

Supported by

Project supported by the Natural Science Foundation of Shandong Province (No. ZR2015YL041).

摘要

一氧化氮(NO)作为生物信使或效应分子在体内发挥重要的生理作用,因其具有多种多样的生物活性在临床应用方面得到广泛关注. 体内NO生成不足常与多种疾病的形成密切相关,NO供体化合物可以通过在体内释放NO治疗和预防多种疾病. 随着NO供体化合物的广泛应用,其合成方法引起了国内外研究人员的高度重视. 结合国内外学者对这方面的研究,对近10年NO供体化合物的合成方法研究进展进行综述.

本文引用格式

王兵 , 李娜 , 刘腾 , 王英爱 , 王晓静 , 孙捷 . 一氧化氮供体化合物的合成方法研究进展[J]. 有机化学, 2017 , 37(4) : 777 -797 . DOI: 10.6023/cjoc201610035

Abstract

Nitric oxide as a biological messenger or effector molecule plays an important physiological role in the body. Owing to its various biological activities, it has received wide attention in clinical practice. Insufficient NO production in vivo is closely related with a variety of diseases. NO donor compounds can release NO in vivo to treat and prevent many diseases. With its wide application in medicine, the methods for the synthesis of NO donor compounds have attracted much attention of researchers. In this paper, the recent advances in the past 10 years in synthetic methods for NO donor compounds are reviewed.

参考文献

[1] Azizzadeh, B.; Yip, H. T.; Blackwell, K. E.; Horvath, S.; Calcaterra, T. C.; Buga, G. M. Laryngoscope 2001, 111, 1896.
[2] Huerta, S.; Chilka, S.; Bonavida, B. Int. J. Oncol. 2008, 33, 909.
[3] Agurla, S.; Gayatri, G.; Raghavendra, A. S. Nitric Oxide 2014, 43, 89.
[4] Jin, R. C.; Loscalzo, J. J. Blood Med. 2010, 2010, 147.
[5] Esplugues, J. V. Br. J. Pharmacol. 2002, 135, 1079.
[6] Wallace, J. L. Mem. Inst. Oswaldo Cruz 2005, 100(suppl. 1), 5.
[7] David, H.; Tracy, R. J. Pharm. Pharmacol. 2007, 59, 3.
[8] Afshar, J. K.; Pluta, R. M.; Boock, R. J.; Thompson, B. G.; Oldfield, E. H. J. Neurosurg. 1995, 83, 118.
[9] Rajagopalan, S.; Harrison, D. G. Circulation 1996, 94, 240.
[10] Steudel, W.; Scherrer-Crosbie, M.; Bloch, K. D.; Weimann, J.; Huang, P. L.; Jones, R. C. J. Clin. Invest. 1998, 101, 2468.
[11] Suzuki, H.; Shimosegawa, T.; Ohara, S.; Toyota, T. J. Gastroenterol. 1999, 34, 172.
[12] Kuo, P. C.; Schroeder, R. A. Ann. Surg. 1995, 221, 220.
[13] Bradley, S. A.; Steinert, J. R. J. Neurosci. Methods 2015, 245, 116.
[14] Serafim, R. A.; Primi, M. C.; Trossini, G. H. Curr. Med. Chem. 2012, 19, 386.
[15] Carradori, S.; Mollica, A.; Monte, C. Molecules 2015, 20, 5667.
[16] Bian, H. Y. Ph.D. Dissertation, Shandong University, Shandong, 2011 (in Chinese).
(边海勇, 博士论文, 山东大学, 山东, 2011.)
[17] Abdellatif, K. R.; Chowdhury, M. A.; Dong, Y.; Das, D.; Yu, G.; Velazquez, C. A.; Suresh, M. R.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2009, 19, 3014.
[18] Abuo-Rahma, E. D. A. A.; Abdel-Aziz, M.; Mai, A. E. M.; Farag, H. H. Bioorg. Med. Chem. 2012, 20, 195.
[19] Luo, G.; Chen, Y. Y. Chin. J. New Drugs 2010, 19, 1322 (in Chinese).
(罗刚, 陈宇瑛, 中国新药杂志, 2010, 19, 1322.)
[20] López, G. V.; Blanco, F.; Hernández, P.; Ferreira, A.; Piro, O. E.; Batthyány, C.; González, M.; Rubbo, H.; Cerecetto, H. Bioorg. Med. Chem. 2007, 15, 6262.
[21] Abdel-Hafez, E. S. M. N.; Abuo-Rahma, E. D. A. A.; Abdel-Aziz, M.; Radwan, M. F.; Farag, H. Bioorg. Med. Chem. 2009, 17, 3829.
[22] Rolando, B.; Filieri, A.; Chegaev, K.; Lazzarato, L.; Giorgis, M.; De Nardi, C.; Fruttero, R.; Martel, S.; Carrupt, P. A.; Gasco, A. Bioorg. Med. Chem. 2012, 20, 841.
[23] Digiacomo, M.; Martelli, A.; Testai, L.; Lapucci, A.; Breschi, M. C.; Calderone, V.; Rapposelli, S. Bioorg. Med. Chem. 2015, 23, 422.
[24] Konter, J.; Mollmann, U.; Lehmann, J. Bioorg. Med. Chem. 2008, 16, 8294.
[25] Bertinaria, M.; Rolando, B.; Giorgis, M.; Montanaro, G.; Marini, E.; Collino, M.; Benetti, E.; Daniele, P. G.; Fruttero, R.; Gasco, A. Eur. J. Med. Chem. 2012, 54, 103.
[26] Biava, M.; Battilocchio, C.; Poce, G.; Alfonso, S.; Consalvi, S.; Di Capua, A.; Calderone, V.; Martelli, A.; Testai, L.; Sautebin, L.; Rossi, A.; Ghelardini, C.; Di Cesare Mannelli, L.; Giordani, A.; Persiani, S.; Colovic, M.; Dovizio, M.; Patrignani, P.; Anzini, M. Bioorg. Med. Chem. 2014, 22, 772.
[27] Liu, W.; Liu, C.; Gong, C.; Lin, W.; Guo, C. Bioorg. Med. Chem. Lett. 2009, 19, 1647.
[28] Peng, S. M.; Zou, X. Q.; Ding, H. L.; Ding, Y. L.; Lin, Y. B. Bioorg. Med. Chem. Lett. 2009, 19, 1264.
[29] Dong, X.; Du, L.; Pan, Z.; Liu, T.; Yang, B.; Hu, Y. Eur. J. Med. Chem. 2010, 45, 3986.
[30] Zou, X. Q.; Peng, S. M.; Hu, C. P.; Tan, L. F.; Yuan, Q.; Deng, H. W.; Li, Y. J. Bioorg. Med. Chem. 2010, 18, 3020.
[31] Bai, R.; Yang, X.; Zhu, Y.; Zhou, Z.; Xie, W.; Yao, H.; Jiang, J.; Liu, J.; Shen, M.; Wu, X.; Xu, J. Bioorg. Med. Chem. 2012, 20, 6848.
[32] Wang, Q. Q.; Cheng, N.; Zheng, X. W.; Peng, S. M.; Zou, X. Q. Bioorg. Med. Chem. 2013, 21, 4301.
[33] Bhandari, S. V.; Bothara, K. G.; Patil, A. A.; Chitre, T. S.; Sarkate, A. P.; Gore, S. T.; Dangre, S. C.; Khachane, C. V. Bioorg. Med. Chem. 2009, 17, 390.
[34] Bhandari, S. V.; Dangre, S. C.; Bothara, K. G.; Patil, A. A.; Sarkate, A. P.; Lokwani, D. K.; Gore, S. T.; Deshmane, B. J.; Raparti, V. T.; Khachane, C. V. Eur. J. Med. Chem. 2009, 44, 4622.
[35] Mourad, M. A.; Abdel-Aziz, M.; Abuo-Rahma Gel, D.; Farag, H. H. Eur. J. Med. Chem. 2012, 54, 907.
[36] Fang, L.; Feng, M.; Chen, F. Bioorg. Med. Chem. 2016, 24, 4611.
[37] Zhang, Y. C.; Zhou, J. P.; Wu, X. M.; Pan, W. H. Chin. Chem. Lett. 2009, 20, 302.
[38] Tamboli, Y.; Lazzarato, L.; Marini, E.; Guglielmo, S.; Novelli, M.; Beffy, P.; Masiello, P.; Fruttero, R.; Gasco, A. Bioorg. Med. Chem. Lett. 2012, 22, 3810.
[39] Kutty, S. K.; Barraud, N.; Pham, A.; Iskander, G.; Rice, S. A.; Black, D. S.; Kumar, N. J. Med. Chem. 2013, 56, 9517.
[40] Huang, Q.; Rui, E. Y.; Cobbs, M.; Dinh, D. M.; Gukasyan, H. J.; Lafontaine, J. A.; Mehta, S.; Patterson, B. D.; Rewolinski, D. A.; Richardson, P. F.; Edwards, M. P. J. Med. Chem. 2015, 58, 2821.
[41] Abdellatif, K. R.; Chowdhury, M. A.; Dong, Y.; Chen, Q. H.; Knaus, E. E. Bioorg. Med. Chem. 2008, 16, 3302.
[42] Kaur, J.; Bhardwaj, A.; Huang, Z.; Narang, D.; Chen, T. Y.; Plane, F.; Knaus, E. E. J. Med. Chem. 2012, 55, 7883.
[43] Xu, G. G.; Deshpande, T. M.; Ghatge, M. S.; Mehta, A. Y.; Omar, A. S.; Ahmed, M. H.; Venitz, J.; Abdulmalik, O.; Zhang, Y.; Safo, M. K. Biochemistry 2015, 54, 7178.
[44] Gazzano, E.; Chegaev, K.; Rolando, B. Bioorg. Med. Chem. 2016, 24, 967.
[45] Fang, L. A. D.; Decker, M.; Kiehntopf, M.; Roegler, C.; Deufel, T.; Fleck, C.; Peng, S. X.; Zhang, Y. H.; Lehmann, J. J. Med. Chem. 2008, 51, 4.
[46] Chowdhury, M. A.; Abdellatif, K. R.; Dong, Y.; Yu, G.; Huang, Z.; Rahman, M.; Das, D.; Velazquez, C. A.; Suresh, M. R.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2010, 20, 1324.
[47] Bertinaria, M.; Guglielmo, S.; Rolando, B.; Giorgis, M.; Aragno, C.; Fruttero, R.; Gasco, A.; Parapini, S.; Taramelli, D.; Martins, Y. C.; Carvalho, L. J. Eur. J. Med. Chem. 2011, 46, 1757.
[48] Zhao, J.; Prosser, K. E.; Chang, S. W. Dalton Trans. 2016, 45, 18079.
[49] Csont, T.; Ferdinandy, P. Pharmacol. Ther. 2005, 105, 57.
[50] Feelisch, M.; Schonafinger, K.; Noack, E. Biochem. Pharmacol. 1992, 44, 1149.
[51] Chen, L. Z. Y.; Kong, X. W.; Lan, E. D.; Huang, Z. J.; Peng, S. X.; Kaufman, D. L.; Tian, J. J. Med. Chem. 2008, 51, 4834.
[52] Ling, Y.; Ye, X.; Ji, H.; Zhang, Y.; Lai, Y.; Peng, S.; Tian, J. Bioorg. Med. Chem. 2010, 18, 3448.
[53] Shi, J. B.; Xu, S.; Wang, Y. P.; Li, J. J.; Yao, Q. Z. Chin. Chem. Lett. 2011, 22, 899.
[54] Tang, W.; Xie, J.; Xu, S.; Lv, H.; Lin, M.; Yuan, S.; Bai, J.; Hou, Q.; Yu, S. J. Med. Chem. 2014, 57, 7600.
[55] Dos Santos, J. L.; Lanaro, C.; Chelucci, R. C.; Gambero, S.; Bosquesi, P. L.; Reis, J. S.; Lima, L. M.; Cerecetto, H.; Gonzalez, M.; Costa, F. F.; Chung, M. C. J. Med. Chem. 2012, 55, 7583.
[56] Bertinaria, M.; Orjuelasanchez, P.; Marini, E. J. Med. Chem. 2015, 58, 7895.
[57] Bian, H.; Feng, J.; Li, M.; Xu, W. Bioorg. Med. Chem. Lett. 2011, 21, 7025.
[58] Borretto, E.; Lazzarato, L.; Spallotta, F.; Cencioni, C.; D'Alessandra, Y.; Gaetano, C.; Fruttero, R.; Gasco, A. ACS Med. Chem. Lett. 2013, 4, 994.
[59] Lu, M.-D.; Zhou, X.; Yu, Y.-J.; Li, P.-H.; Sun, W.-J.; Zhao, C.-G.; Zheng, Z.-Q.; You, T.; Wang, F.-H. Chin. Chem. Lett. 2013, 24, 415.
[60] Ai, Y.; Kang, F.; Huang, Z.; Xue, X.; Lai, Y.; Peng, S.; Tian, J.; Zhang, Y. J. Med. Chem. 2015, 58, 2452.
[61] Duan, W.; Li, J.; Inks, E. S.; Chou, C. J.; Jia, Y.; Chu, X.; Li, X.; Xu, W.; Zhang, Y. J. Med. Chem. 2015, 58, 4325.
[62] Massarico Serafim, R. A.; Goncalves, J. E.; de Souza, F. P.; de Melo Loureiro, A. P.; Storpirtis, S.; Krogh, R.; Andricopulo, A. D.; Dias, L. C.; Ferreira, E. I. Eur. J. Med. Chem. 2014, 82, 418.
[63] Lakshman, T. R.; Deb, J.; Paine, T. K. Dalton Trans. 2016, 45, 14053.
[64] Davies, K. M.; Wink, D. A.; Saavedra, J. E.; Keefer, L. K. J. Am. Chem. Soc. 2001, 32, 5473.
[65] Smith, D. J.; Chakravarthy, D.; Pulfer, S.; Simmons, M. L.; Hrabie, J. A.; Citro, M. L. J. Med. Chem. 1996, 39, 1148.
[66] Chakrapani, H.; Goodblatt, M. M.; Udupi, V.; Malaviya, S.; Shami, P. J.; Keefer, L. K.; Saavedra, J. E. Bioorg. Med. Chem. Lett. 2008, 18, 950.
[67] Chowdhury, M. A.; Abdellatif, K. R.; Dong, Y.; Knaus, E. E. Bioorg. Med. Chem. 2008, 16, 8882.
[68] Abdellatif, K. R.; Moawad, A.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2014, 24, 5015.
[69] Abdellatif, K. R.; Chowdhury, M. A.; Velazquez, C. A.; Huang, Z.; Dong, Y.; Das, D.; Yu, G.; Suresh, M. R.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2010, 20, 4544.
[70] Abdellatif, K. R.; Chowdhury, M. A.; Dong, Y.; Knaus, E. E. Bioorg. Med. Chem. 2008, 16, 6528.
[71] Abdellatif, K. R.; Chowdhury, M. A.; Dong, Y.; Velazquez, C.; Das, D.; Suresh, M. R.; Knaus, E. E. Bioorg. Med. Chem. 2008, 16, 9694.
[72] Abdellatif, K. R.; Huang, Z.; Chowdhury, M. A.; Kaufman, S.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2011, 21, 3951.
[73] Velázquez, C. A.; Chen, Q. H.; Citro, M. L.; Keefer, L. K.; Knaus, E. E. J. Med. Chem. 2008, 51, 1954.
[74] Xu, S.; Wang, G.; Yan, L. Bioorg. Med. Chem. Lett. 2016, 26, 2795.
[75] Abdellatif, K. R.; Chowdhury, M. A.; Dong, Y.; Das, D.; Yu, G.; Velazquez, C.; Suresh, M. R.; Knaus, E. E. Bioorg. Med. Chem. 2009, 17, 5182.
[76] Smirnov, G. A.; Gordeev, P. B.; Nikitin, S. V. Russ. Chem. Bull. 2014, 63, 487.
[77] Abuo-Rahma, E. D. A. A.; Abdel-Aziz, M.; Beshr, E. A.; Ali, T. F. Eur. J. Med. Chem. 2014, 71, 185.
[78] Cassien, M.; Petrocchi, C.; Thétiot-Laurent, S. Eur. J. Med. Chem. 2016, 119, 197.
[79] Vogt, M. A.; Vogel, A. S.; Pfeiffer, N.; Gass, P.; Inta, D. Eur. Neuropsychopharmacol. 2015, 25, 1848.
[80] Mcquilken, A. C.; Yang, H.; Sutherlin, K. D.; Siegler, M. A.; Hodgson, K. O.; Britt, H. J. Am. Chem. Soc. 2013, 135, 14024.
[81] Sanina, N. A.; Kozub, G. I.; Kondratéva, T. A.; Korchagin, D. V.; Shilov, G. V.; Emelýanova, N. S. J. Mol. Struct. 2014, 1075, 159.
[82] Monti, M.; Ciccone, V.; Pacini, A. Pharmacol. Res. 2016, 107, 352.
[83] Sakhaei, Z.; Kundu, S.; Donnelly, J. Chem. Commun. 2017, 53, 549.
[84] Kumar, R.; Kumar, S.; Bala, M. RSC Adv. 2016, 6, 72096.
[85] Grossi, L.; Montevecchi, P. C. J. Org. Chem. 2002, 67, 8625.
[86] Kumari, S.; Sammut, I. A.; Giles, G. I. Eur. J. Med. Chem. 2014, 737, 168.
[87] Stasko, N. A.; Fischer, T. H.; Schoenfisch, M. H. Biomacromolecules 2008, 9, 834.
[88] Llop, J.; Gómez-Vallejo, V.; Bosque, M.; Quincoces, G.; Peñuelas, I. Appl. Radiat. Isot. 2009, 67, 95.
[89] Priora, R.; Margaritis, A.; Frosali, S.; Coppo, L.; Summa, D.; Giuseppe, D. D. Pharmacol. Res. 2011, 64, 289.
[90] Ming, X.; Noriko, F.; Zhong, W.; Tingwei, C.; Satoshi, K.; Janczuk, A. J. Bioorg. Med. Chem. 2002, 10, 3049.
[91] Tyagi, A. K.; Cooney, D. A. Adv. Pharmacol. Chemother. 1984, 20, 69.

文章导航

/