伊必那班

伊必那班
臨床資料
ATC碼
  • 未分配
识别信息
  • 4S-(−)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine
CAS号464213-10-3  checkY
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)
ECHA InfoCard100.158.931 編輯維基數據鏈接
化学信息
化学式C24H22Cl2N4O2S
摩尔质量501.427
3D模型（JSmol（英语：JSmol））
  • c2cc(Cl)ccc2C1=NN(C(NC)=NCS(=O)(=O)c3ccc(Cl)cc3)CC1c4ccccc4
  • InChI=1S/C24H22Cl2N4O2S/c1-27-24(28-16-33(31,32)21-13-11-20(26)12-14-21)30-15-22(17-5-3-2-4-6-17)23(29-30)18-7-9-19(25)10-8-18/h2-14,22H,15-16H2,1H3,(H,27,28)/t22-/m1/s1 ☒N
  • Key:BSFKAVCGRDMWTK-JOCHJYFZSA-N ☒N

伊必那班（英语：Ibipinabant；开发代号：SLV319、BMS-646,256) 是一种用于科学研究的药物，可作为强效和高选择性的大麻素受体1（CB1）拮抗剂。[1]它对动物有强烈的厌食作用，[2]并被研究用于治疗肥胖症，CB1拮抗剂作为一类药物由于利莫那班出现的问题而不再受青睐，因此伊比那班现在仅用于实验室研究，特别是对新型CB1拮抗剂的构效关系研究。[3][4][5]SLV330是伊必那班的结构类似物，据报道其在与记忆、认知以及成瘾行为调节相关的动物模型中具有活性。[6][7]已报道了伊必那班的原子效率合成。[8]

参见

参考资料

  1. ^ Lange JH, Coolen HK, van Stuivenberg HH, Dijksman JA, Herremans AH, Ronken E, et al. Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists. Journal of Medicinal Chemistry. January 2004, 47 (3): 627–43. PMID 14736243. doi:10.1021/jm031019q. 
  2. ^ Need AB, Davis RJ, Alexander-Chacko JT, Eastwood B, Chernet E, Phebus LA, et al. The relationship of in vivo central CB1 receptor occupancy to changes in cortical monoamine release and feeding elicited by CB1 receptor antagonists in rats. Psychopharmacology. January 2006, 184 (1): 26–35. PMID 16328376. S2CID 23402768. doi:10.1007/s00213-005-0234-x. 
  3. ^ Lange JH, van Stuivenberg HH, Veerman W, Wals HC, Stork B, Coolen HK, et al. Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity. Bioorganic & Medicinal Chemistry Letters. November 2005, 15 (21): 4794–8. PMID 16140010. doi:10.1016/j.bmcl.2005.07.054. 
  4. ^ Srivastava BK, Joharapurkar A, Raval S, Patel JZ, Soni R, Raval P, et al. Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism: synthesis, biological evaluation, and molecular modeling in the homology model. Journal of Medicinal Chemistry. November 2007, 50 (24): 5951–66. PMID 17979261. doi:10.1021/jm061490u. 
  5. ^ Srivastava BK, Soni R, Joharapurkar A, Sairam KV, Patel JZ, Goswami A, et al. Bioisosteric replacement of dihydropyrazole of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole. Bioorganic & Medicinal Chemistry Letters. February 2008, 18 (3): 963–8. PMID 18207393. doi:10.1016/j.bmcl.2007.12.036. 
  6. ^ de Bruin, NMWJ; Prickaerts, J; Lange, JHM; Akkerman, S; Andriambeloson, E; de Haan, M; Wijnen, J; van Drimmelen, M; Hissink, E; Heijink, L; Kruse, CG. SLV330, a cannabinoid CB1 receptor antagonist, ameliorates deficits in the T-maze, object recognition and Social Recognition Tasks in rodents. Neurobiology of Learning and Memory. 2010, 93 (4): 522–531. PMID 20132903. S2CID 207261719. doi:10.1016/j.nlm.2010.01.010 （英语）. 
  7. ^ de Bruin, NMWJ; Lange, JHM; Kruse, CG; Herremans, AH; Schoffelmeer, ANM; van Drimmelen, M; De Vries, TJ. SLV330, a cannabinoid CB1 receptor antagonist, attenuates ethanol and nicotine seeking and improves inhibitory response control in rats. Behavioural Brain Research. 2011, 217 (2): 408–415. PMID 21074574. S2CID 205882042. doi:10.1016/j.bbr.2010.11.013 （英语）. 
  8. ^ Lange, JHM; Sanders, HJ; van Rheenen, J. An expedient atom-efficient synthesis of the cannabinoid CB1 receptor inverse agonist ibipinabant. Tetrahedron Letters. 2011, 52 (12): 1303–1305. ISSN 0040-4039. doi:10.1016/j.tetlet.2011.01.068 （英语）.