7-氯氯卡色林

7-氯氯卡色林
臨床資料
其他名稱	7-Cl-lorcaserin
藥物類別	Serotonin 5-HT2 receptor agonist
ATC碼	未分配;
识别信息
	IUPAC命名法 (1R)-7,8-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; ;
PubChem CID	24773649;
ChemSpider	23309887;
ChEMBL	ChEMBL253591;
化学信息
化学式	C11H13Cl2N
摩尔质量	230.13 g·mol−1
3D模型（JSmol）	交互式图像;
	SMILES C[C@H]1CNCCC2=CC(=C(C=C12)Cl)Cl;
	InChI InChI=1S/C11H13Cl2N/c1-7-6-14-3-2-8-4-10(12)11(13)5-9(7)8/h4-5,7,14H,2-3,6H2,1H3/t7-/m0/s1; Key:KTCVEIAEKPSBCJ-ZETCQYMHSA-N;

7-氯氯卡色林，化学名(1R)-7,8-二氯-1-甲基-2,3,4,5-四氢-1H-3-苯并氮杂环庚三烯，是一种有机化合物，化学式为C₁₁H₁₃Cl₂N。它是一种一种血清素 5-HT₂受体激动剂。它是食欲抑制剂和减肥药氯卡色林（英语：lorcaserin）（Belviq）的结构类似物，最初于2005年被文献报道。^[1]^[2]^[3]

参考文献

^ Shah, J. H., Hindupur, R. M., & N Pati, H. (2015). Pharmacological and biological activities of benzazepines: An overview. Current Bioactive Compounds, 11(3), 170–188. https://doi.org/10.2174/1573407211666150910202200 "A series of 3-benzazepines was synthesized by Smith Jeffrey and Smith Brian [134]. These benzazepine act as modulators of 5-HT2C receptors and provide a number of potent and selective 5-HT2C receptor agonists. The functional activity of the compounds at the h5-HT2C (INI isoform), h5-HT2A, and h5-HT2B receptors is determined by measurement of [3H]-phosphoinositol turnover in transiently transfected HEK-293 cells. Lorcaserin (Fig. 17) acts as an anorectic and have serotonergic properties. It is a selective 5- HT2C receptor agonist and the drug showed reasonable selectivity for 5-HT2C over other related targets during in vivo and in vitro testing [135, 136]. It has shown 100x selectivity for 5-HT2C (EC50=39 nM) versus the closely related 5-HT2B (EC50=2380 nM) receptor, and 17x selectivity over the 5- HT2A (EC50= 553 nM) receptor. [...] When substituent at 7-position was added in lorcaserin, it increased 5-HT2C potency and even greatly increased in 5-HT2A and 5-HT2B receptor potencies resulting in reduced selectivity. [...]"
^ Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, Chen RR, Park DM, Prieto EB, Gallardo CS, Sengupta D, Thomsen WJ, Saldana HR, Whelan KT, Menzaghi F, Webb RR, Beeley NR. Discovery and SAR of new benzazepines as potent and selective 5-HT(2C) receptor agonists for the treatment of obesity. Bioorganic & Medicinal Chemistry Letters. March 2005, 15 (5): 1467–1470. PMID 15713408. doi:10.1016/j.bmcl.2004.12.080.
^ Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, Chen RR, Park DM, Prieto EB, Gallardo CS, Sengupta D, Dosa PI, Covel JA, Ren A, Webb RR, Beeley NR, Martin M, Morgan M, Espitia S, Saldana HR, Bjenning C, Whelan KT, Grottick AJ, Menzaghi F, Thomsen WJ. Discovery and structure-activity relationship of (1R)-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (Lorcaserin), a selective serotonin 5-HT2C receptor agonist for the treatment of obesity. Journal of Medicinal Chemistry. January 2008, 51 (2): 305–313. PMID 18095642. doi:10.1021/jm0709034.

[ShahHindupurPati2015-1] Shah, J. H., Hindupur, R. M., & N Pati, H. (2015). Pharmacological and biological activities of benzazepines: An overview. Current Bioactive Compounds, 11(3), 170–188. https://doi.org/10.2174/1573407211666150910202200 "A series of 3-benzazepines was synthesized by Smith Jeffrey and Smith Brian [134]. These benzazepine act as modulators of 5-HT2C receptors and provide a number of potent and selective 5-HT2C receptor agonists. The functional activity of the compounds at the h5-HT2C (INI isoform), h5-HT2A, and h5-HT2B receptors is determined by measurement of [3H]-phosphoinositol turnover in transiently transfected HEK-293 cells. Lorcaserin (Fig. 17) acts as an anorectic and have serotonergic properties. It is a selective 5- HT2C receptor agonist and the drug showed reasonable selectivity for 5-HT2C over other related targets during in vivo and in vitro testing [135, 136]. It has shown 100x selectivity for 5-HT2C (EC50=39 nM) versus the closely related 5-HT2B (EC50=2380 nM) receptor, and 17x selectivity over the 5- HT2A (EC50= 553 nM) receptor. [...] When substituent at 7-position was added in lorcaserin, it increased 5-HT2C potency and even greatly increased in 5-HT2A and 5-HT2B receptor potencies resulting in reduced selectivity. [...]"

[Smith_2005-2] Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, Chen RR, Park DM, Prieto EB, Gallardo CS, Sengupta D, Thomsen WJ, Saldana HR, Whelan KT, Menzaghi F, Webb RR, Beeley NR. Discovery and SAR of new benzazepines as potent and selective 5-HT(2C) receptor agonists for the treatment of obesity. Bioorganic & Medicinal Chemistry Letters. March 2005, 15 (5): 1467–1470. PMID 15713408. doi:10.1016/j.bmcl.2004.12.080.

[Smith_2008-3] Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, Chen RR, Park DM, Prieto EB, Gallardo CS, Sengupta D, Dosa PI, Covel JA, Ren A, Webb RR, Beeley NR, Martin M, Morgan M, Espitia S, Saldana HR, Bjenning C, Whelan KT, Grottick AJ, Menzaghi F, Thomsen WJ. Discovery and structure-activity relationship of (1R)-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (Lorcaserin), a selective serotonin 5-HT2C receptor agonist for the treatment of obesity. Journal of Medicinal Chemistry. January 2008, 51 (2): 305–313. PMID 18095642. doi:10.1021/jm0709034.

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