2-[4-(dimethylamino)phenyl]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol | 1189352-91-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[4-(dimethylamino)phenyl]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol
• CAS: 1189352-91-7
• 化学式: C₁₅H₁₈N₂OS
• 分子量: 274.387
• InChiKey: HMANXAFVUFXDNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  480.7±55.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(dimethylamino)phenyl]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol 生成 (R)-2-[4-(dimethylamino)phenyl]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol 、 (S)-2-[4-(dimethylamino)phenyl]-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：

  7-氧杂二环[4.1.0]庚烷-2-酮 、 4-二甲基氨基硫代苯胺 以 甲醇 为溶剂， 反应 18.0h， 以45%的产率得到2-[4-(dimethylamino)phenyl]-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

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 DE 2-HÉTÉROARYL-THIAZOLYLE, LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：WYETH CORP

  公开号：WO2009120826A1

  公开（公告）日：2009-10-01

  The present invention discloses fused bicyclic 2-aryl- or 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, including elevated securin levels.

  本发明揭示了融合的双环2-芳基或2-杂环芳基噻唑基化合物及其药用盐和酯，这些化合物对抑制癌细胞的生长、特别是抑制人类乳腺癌肿瘤的生长以及治疗与分泌蛋白相关的疾病或紊乱，包括高水平的分泌蛋白水平具有用处。
• 2-Aryl- and 2-Heteroarylthiazolyl Compounds, Methods for Their Preparation and Use Thereof
  申请人：Zhang Nan

  公开号：US20090270363A1

  公开（公告）日：2009-10-29

  The present invention discloses fused bicyclic 2-aryl- or 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, including elevated securin levels.

  本发明公开了融合的双环2-芳基-或2-杂环基硫唑基化合物及其药学上可接受的盐和酯，其对抑制癌细胞生长、特别是对抑制人类乳腺癌肿瘤生长以及治疗与分离素有关的疾病或疾病相关障碍，包括升高的分离素水平具有用处。
• 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.