5-iodothiophene-3-carboxylic acid | 18895-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-iodothiophene-3-carboxylic acid
• CAS: 18895-01-7
• 化学式: C₅H₃IO₂S
• mdl: MFCD14705903
• 分子量: 254.048
• InChiKey: RBTHAHOQJNQFNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-iodothiophene-3-carboxylic acid 在 六甲基磷酰三胺 、 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 5-(trifluoromethyl)thiophene-3-carboxylate
  参考文献：
  名称：

  [EN] BENZIMIDAZOLE DERIVATIVES AS MCH RECEPTOR ANTAGONISTS
  [FR] DÉRIVÉS DE BENZIMIDAZOLE COMME ANTAGONISTES DU RÉCEPTEUR MCH

  摘要：

  本发明提供了一种具有黑色素浓集激素受体拮抗作用并且用作预防或治疗肥胖等疾病的芳香环化合物。本发明涉及一种由式(I)表示的化合物，其中每个符号如规范中定义的，或其盐。

  公开号：

  WO2013105676A1

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES AS MCH RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE COMME ANTAGONISTES DU RÉCEPTEUR MCH
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2013105676A1

  公开（公告）日：2013-07-18

  The present invention provides an aromatic ring compound having a melanin-concentrating hormone receptor antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula (I) wherein each symbol as defined in the specification, or a salt thereof.

  本发明提供了一种具有黑色素浓集激素受体拮抗作用并且用作预防或治疗肥胖等疾病的芳香环化合物。本发明涉及一种由式(I)表示的化合物，其中每个符号如规范中定义的，或其盐。
• BENZIMIDAZOLE DERIVATIVES AS MCH RECEPTOR ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20150018363A1

  公开（公告）日：2015-01-15

  The present invention provides an aromatic ring compound having a melanin-concentrating hormone receptor antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula wherein each symbol as defined in the specification, or a salt thereof.

  本发明提供了一种具有黑色素浓缩激素受体拮抗作用的芳香环化合物，可用作预防或治疗肥胖等药物。本发明涉及一种由式中定义的每个符号或其盐所表示的化合物。
• Benzimidazole derivatives as MCH receptor antagonists
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US09365540B2

  公开（公告）日：2016-06-14

  The present invention provides an aromatic ring compound having a melanin-concentrating hormone receptor antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula wherein each symbol as defined in the specification, or a salt thereof.

  本发明提供了一种具有黑色素浓缩激素受体拮抗作用的芳香环化合物，可用作预防或治疗肥胖等疾病的药剂。本发明涉及一种由式中定义的每个符号或其盐表示的化合物。
• Spinelli, Domenico; Lamartina, Liliana; Noto, Renato, Journal of Chemical Research, Miniprint, 1993, # 8, p. 1873 - 1890
  作者：Spinelli, Domenico、Lamartina, Liliana、Noto, Renato、Consiglio, Giovanni、Chimichi, Stefano

  DOI：——

  日期：——
• Amine-free melanin-concentrating hormone receptor 1 antagonists: Novel non-basic 1-(2H-indazole-5-yl)pyridin-2(1H)-one derivatives and mitigation of mutagenicity in Ames test
  作者：Hideyuki Igawa、Masashi Takahashi、Minoru Ikoma、Hiromi Kaku、Keiko Kakegawa、Asato Kina、Jumpei Aida、Shoki Okuda、Yayoi Kawata、Toshihiro Noguchi、Natsu Hotta、Syunsuke Yamamoto、Masaharu Nakayama、Yasutaka Nagisa、Shizuo Kasai、Tsuyoshi Maekawa

  DOI：10.1016/j.bmc.2016.04.013

  日期：2016.6

  To develop non-basic melanin-concentrating hormone receptor 1 (MCHR1) antagonists with a high probability of target selectivity and therapeutic window, we explored neutral bicyclic motifs that could replace the previously reported imidazo[1,2-a]pyridine or 1H-benzimidazole motif. The results indicated that the binding affinity of a chemically neutral 2H-indazole derivative 8a with MCHR1 (hMCHR1: IC50 = 35 nM) was comparable to that of the imidazopyridine and benzimidazole derivatives (1 and 2, respectively) reported so far. However, 8a was positive in the Ames test using TA1537 in S9- condition. Based on a putative intercalation of 8a with DNA, we introduced a sterically-hindering cyclopropyl group on the indazole ring to decrease planarity, which led to the discovery of 1-(2-cyclopropyl-3-methyl-2H-indazol- 5-yl)-4-[5-(trifluoromethyl)thiophen-3-yl]methoxy} pyridin-2(1H)-one 8l without mutagenicity in TA1537. Compound 8l exerted significant antiobesity effects in diet-induced obese F344 rats and exhibited promising safety profile. (C) 2016 Elsevier Ltd. All rights reserved.