4-(Pyrrolidin-1-yl)benzene-1-carbothioamide | 792892-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(Pyrrolidin-1-yl)benzene-1-carbothioamide
• 英文别名: 4-pyrrolidin-1-ylbenzenecarbothioamide
• CAS: 792892-62-7
• 化学式: C₁₁H₁₄N₂S
• 分子量: 206.312
• InChiKey: WFFNXOCVGQVAJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-氧杂二环[4.1.0]庚烷-2-酮 、 4-(Pyrrolidin-1-yl)benzene-1-carbothioamide 以 甲醇 为溶剂， 反应 18.0h， 生成 2-(4-pyrrolidin-1-ylphenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol
  参考文献：
  名称：

  2-Aryl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols as a class of antitumor agents selectively active in securin−/− cells

  摘要：

  A series of 2-(4-aminophenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols have been developed as antitumor agents that showed high selectivity against aneuploid cell lines (vs diploid cell lines). Structure-activity relationship studies showed that a hydroxymethyl group at the 2- position of the phenyl ring increased potency and selectivity. A pyrrolidinyl group at the 4-position of the phenyl ring was comparable to a dimethylamino group. The corresponding 5-aza analogs, 2-(4-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridin-7-ols, retained potency and high level of selectivity against aneuploid cell growth (vs diploid cells). These 5-aza compounds exhibited higher water solubility and higher metabolic stability than the corresponding carba analogs. Compound 19 showed the highest potency against MCF-7 and MDA-MB-361 lines and was selected for further evaluation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.021
• 作为产物：
  描述：

  4-(1-吡咯烷)苯甲腈 在 tetraphosphorus decasulfide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 4-(Pyrrolidin-1-yl)benzene-1-carbothioamide
  参考文献：
  名称：

  2-Aryl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols as a class of antitumor agents selectively active in securin−/− cells

  摘要：

  A series of 2-(4-aminophenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols have been developed as antitumor agents that showed high selectivity against aneuploid cell lines (vs diploid cell lines). Structure-activity relationship studies showed that a hydroxymethyl group at the 2- position of the phenyl ring increased potency and selectivity. A pyrrolidinyl group at the 4-position of the phenyl ring was comparable to a dimethylamino group. The corresponding 5-aza analogs, 2-(4-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridin-7-ols, retained potency and high level of selectivity against aneuploid cell growth (vs diploid cells). These 5-aza compounds exhibited higher water solubility and higher metabolic stability than the corresponding carba analogs. Compound 19 showed the highest potency against MCF-7 and MDA-MB-361 lines and was selected for further evaluation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.021

文献信息

• [EN] 2-ARYL- AND 2-HETEROARYLTHIAZOLYL COMPOUNDS, METHODS FOR THEIR PREPARATION AND USE THEREOF<br/>[FR] COMPOSÉS DE 2-ARYL- ET 2-HÉTÉROARYLTHIAZOLYLE, ET PROCÉDÉS CORRESPONDANTS D'ÉLABORATION ET D'UTILISATION
  申请人：WYETH CORP

  公开号：WO2009120849A1

  公开（公告）日：2009-10-01

  The present invention discloses fused heterobicyclic 2-aryl- and 2-heteroarylthiazolyl compounds and their pharmaceutically acceptable salts and esters thereof, which are useful for inhibiting the growth of cancerous cells, inhibiting human breast carcinoma tumor growth in particular and to treat diseases or disorders associated with securin (Formula I) and pharmaceutically acceptable salts thereof, wherein A is H, C1-C3 alkyi, or acetyl; Z is NR3 or O; Q is -NR1R2, - NR3N(R3)2. - NR3OR3, or -OH.

  本发明公开了融合的杂双环2-芳基和2-杂芳基噻唑基化合物及其药用可接受的盐和酯，用于抑制癌细胞的生长，特别是抑制人类乳腺癌肿瘤的生长，并用于治疗与蛋白质分离素（化学式I）和其药用可接受的盐相关的疾病或紊乱，其中A为H，C1-C3烷基，或乙酰基；Z为NR3或O；Q为-NR1R2，- NR3N(R3)2，- NR3OR3，或-OH。
• 2-Aryl-and 2-Heteroarylthiazolyl Compounds, Methods for Their Preparation and Use Thereof
  申请人：Zhang Nan

  公开号：US20090270447A1

  公开（公告）日：2009-10-29

  The present invention discloses fused heterobicyclic 2-aryl- and 2-heteroarylthiazolyl compounds and their pharmaceutically acceptable salts and esters thereof, which are useful for inhibiting the growth of cancerous cells, inhibiting human breast carcinoma tumor growth in particular and to treat diseases or disorders associated with securin.

  本发明揭示了熔合的异杂双环2-芳基-和2-杂芳基噻唑基化合物及其药学上可接受的盐和酯，对于抑制癌细胞生长，特别是抑制人乳腺癌肿瘤生长以及治疗与securin相关的疾病或紊乱有用。
• 2-Aryl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols as a class of antitumor agents selectively active in securin−/− cells
  作者：Nan Zhang、Semiramis Ayral-Kaloustian、Chuansheng Niu、Thai Nguyen、Erik Upeslacis、Tarek S. Mansour、Shoba Ragunathan、Edward Rosfjord

  DOI：10.1016/j.bmcl.2010.05.021

  日期：2010.7

  A series of 2-(4-aminophenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ols have been developed as antitumor agents that showed high selectivity against aneuploid cell lines (vs diploid cell lines). Structure-activity relationship studies showed that a hydroxymethyl group at the 2- position of the phenyl ring increased potency and selectivity. A pyrrolidinyl group at the 4-position of the phenyl ring was comparable to a dimethylamino group. The corresponding 5-aza analogs, 2-(4-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridin-7-ols, retained potency and high level of selectivity against aneuploid cell growth (vs diploid cells). These 5-aza compounds exhibited higher water solubility and higher metabolic stability than the corresponding carba analogs. Compound 19 showed the highest potency against MCF-7 and MDA-MB-361 lines and was selected for further evaluation. (c) 2010 Elsevier Ltd. All rights reserved.