2-(2-imino-thiazolidin-3-yl)-1-thiophen-2-yl-ethanone | 86651-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-imino-thiazolidin-3-yl)-1-thiophen-2-yl-ethanone
• 英文别名: 2-(2-Imino-1,3-thiazolan-3-YL)-1-(2-thienyl)-1-ethanone；2-(2-imino-1,3-thiazolidin-3-yl)-1-thiophen-2-ylethanone
• CAS: 86651-24-3
• 化学式: C₉H₁₀N₂OS₂
• mdl: MFCD02634203
• 分子量: 226.323
• InChiKey: JUVUYGMGZLJNLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-imino-thiazolidin-3-yl)-1-thiophen-2-yl-ethanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以42%的产率得到2-(2-imino-thiazolidin-3-yl)-1-thiophen-2-yl-ethanol
  参考文献：
  名称：

  Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase

  摘要：

  Pathological calcifications induced by deposition of basic phosphate crystals or hydroxyapatite (HA) on soft tissues are a large family of diseases comprising of ankylosing spondylitis (AS), end-stage osteoarthritis (OA) and vascular calcification. High activity of tissue non-specific alkaline phosphatase (TNAP) is a hallmark of pathological calcifications induced by HA deposition. The use of TNAP inhibitor is a possible therapeutic option to address calcific diseases produced by HA deposition on soft tissues. We report the synthesis of a series of thiopheno-imidazo[2,1-b] thiazole derivatives which were evaluated as potential inhibitors of TNAP displaying a large range of IC50 at pH 10.4 (from 42 +/- 13 mu M to more than 800 mu M). (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.02.089
• 作为产物：
  描述：

  2-氨基-2-噻唑啉 、 2-溴-1-(2-THIENYL)-1-ETHANONE 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到2-(2-imino-thiazolidin-3-yl)-1-thiophen-2-yl-ethanone
  参考文献：
  名称：

  Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase

  摘要：

  Pathological calcifications induced by deposition of basic phosphate crystals or hydroxyapatite (HA) on soft tissues are a large family of diseases comprising of ankylosing spondylitis (AS), end-stage osteoarthritis (OA) and vascular calcification. High activity of tissue non-specific alkaline phosphatase (TNAP) is a hallmark of pathological calcifications induced by HA deposition. The use of TNAP inhibitor is a possible therapeutic option to address calcific diseases produced by HA deposition on soft tissues. We report the synthesis of a series of thiopheno-imidazo[2,1-b] thiazole derivatives which were evaluated as potential inhibitors of TNAP displaying a large range of IC50 at pH 10.4 (from 42 +/- 13 mu M to more than 800 mu M). (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.02.089

文献信息

• Novel Broad-Spectrum Anthelmintics. Tetramisole¹ and Related Derivatives of 6-Arylimidazo[2,1-b]thiazole
  作者：Alfons H. M. Raeymaekers、Fernand T. N. Allewijn、Jan Vandenberk、Paul J. A. Demoen、Theo T. T. Van Offenwert、Paul A. J. Janssen

  DOI：10.1021/jm00322a023

  日期：1966.7
• [EN] NOVEL BENZOTHIOPHENE DERIVATIVES WITH TNAP-INHIBITING ACTIVITY<br/>[FR] NOUVEAUX DERIVES DE BENZOTHIOPHENE, PRESENTANT UNE ACTIVITE INHIBITRICE DE LA TNAP
  申请人：UNIV CLAUDE BERNARD LYON

  公开号：WO2012052668A1

  公开（公告）日：2012-04-26

  La présente invention concerne des composés de formule (I) : dans laquelle R1, R2, R3, R4, R5, R6, X et Y sont tels que définis à la revendications 1, leur utilisation en tant que médicament, et notamment pour le traitement de l'arthrose ou de calcifications vasculaires, ainsi que les compositions pharmaceutiques les contenant en association avec au moins un excipient pharmaceutiquement acceptable.
• Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase
  作者：Lei Chang、Do Le Duy、Saida Mébarek、Florence Popowycz、Stéphane Pellet-Rostaing、Marc Lemaire、René Buchet

  DOI：10.1016/j.bmcl.2011.02.089

  日期：2011.4

  Pathological calcifications induced by deposition of basic phosphate crystals or hydroxyapatite (HA) on soft tissues are a large family of diseases comprising of ankylosing spondylitis (AS), end-stage osteoarthritis (OA) and vascular calcification. High activity of tissue non-specific alkaline phosphatase (TNAP) is a hallmark of pathological calcifications induced by HA deposition. The use of TNAP inhibitor is a possible therapeutic option to address calcific diseases produced by HA deposition on soft tissues. We report the synthesis of a series of thiopheno-imidazo[2,1-b] thiazole derivatives which were evaluated as potential inhibitors of TNAP displaying a large range of IC50 at pH 10.4 (from 42 +/- 13 mu M to more than 800 mu M). (C) 2011 Published by Elsevier Ltd.