5-Bromo-4-pyrrolidin-1-ylsulfonylthiophene-2-carboxylic acid | 1094668-91-3

• 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-Bromo-4-pyrrolidin-1-ylsulfonylthiophene-2-carboxylic acid
• CAS: 1094668-91-3
• 化学式: C₉H₁₀BrNO₄S₂
• mdl: MFCD11647591
• 分子量: 340.219
• InChiKey: URHKQIYEEPOBGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Bromo-4-pyrrolidin-1-ylsulfonylthiophene-2-carboxylic acid 、 5-氨甲基噻唑 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-bromo-4-(pyrrolidin-1-ylsulfonyl)-N-(thiazol-5-ylmethyl)thiophene-2-carboxamide
  参考文献：
  名称：

  A novel small-molecule inhibitor of IL-6 signalling

  摘要：

  A small library of pyrrolidinesulphonylaryl molecules has been synthesized via an efficient 4-step route, and members evaluated for their ability to inhibit IL-6 signalling. One molecule (6a) was found to have promising activity against IL-6/STAT3 signalling at the low micromolar level, and to selectively inhibit phosphorylation of STAT3 (but not STAT1) in IL-6 stimulated MDA-MB-231 breast cancer and HeLa cell lines. It was also selectively cytostatic in MDA-MB-231 (STAT3-dependent) versus A4 (STAT3-null) cells suggesting STAT3-specific inhibitory properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.117
• 作为产物：
  描述：

  四氢吡咯 、 5-bromo-4-(chlorosulfonyl)thiophene-2-carboxylic acid 以 甲醇 为溶剂， 反应 1.0h， 生成 5-Bromo-4-pyrrolidin-1-ylsulfonylthiophene-2-carboxylic acid
  参考文献：
  名称：

  A novel small-molecule inhibitor of IL-6 signalling

  摘要：

  A small library of pyrrolidinesulphonylaryl molecules has been synthesized via an efficient 4-step route, and members evaluated for their ability to inhibit IL-6 signalling. One molecule (6a) was found to have promising activity against IL-6/STAT3 signalling at the low micromolar level, and to selectively inhibit phosphorylation of STAT3 (but not STAT1) in IL-6 stimulated MDA-MB-231 breast cancer and HeLa cell lines. It was also selectively cytostatic in MDA-MB-231 (STAT3-dependent) versus A4 (STAT3-null) cells suggesting STAT3-specific inhibitory properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.117

文献信息

• A novel small-molecule inhibitor of IL-6 signalling
  作者：Giovanna Zinzalla、Mohammad R. Haque、B. Piku Basu、John Anderson、Samantha L. Kaye、Shozeb Haider、Fyeza Hasan、Dyeison Antonow、Samantha Essex、Khondaker M. Rahman、Jonathan Palmer、Daniel Morgenstern、Andrew F. Wilderspin、Stephen Neidle、David E. Thurston

  DOI：10.1016/j.bmcl.2010.09.117

  日期：2010.12

  A small library of pyrrolidinesulphonylaryl molecules has been synthesized via an efficient 4-step route, and members evaluated for their ability to inhibit IL-6 signalling. One molecule (6a) was found to have promising activity against IL-6/STAT3 signalling at the low micromolar level, and to selectively inhibit phosphorylation of STAT3 (but not STAT1) in IL-6 stimulated MDA-MB-231 breast cancer and HeLa cell lines. It was also selectively cytostatic in MDA-MB-231 (STAT3-dependent) versus A4 (STAT3-null) cells suggesting STAT3-specific inhibitory properties. (C) 2010 Elsevier Ltd. All rights reserved.