2-amino-4-bromo-thiophenol; hydrochloride | 79811-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 2-amino-4-bromo-thiophenol; hydrochloride
• 英文别名: 2-Amino-4-brom-thiophenol; Hydrochlorid；4-bromo-2-aminothiophenol hydrochloride；(5-Bromo-2-sulfanylphenyl)azanium;chloride；(5-bromo-2-sulfanylphenyl)azanium;chloride
• CAS: 79811-34-0
• 化学式: C₆H₆BrNS*ClH
• 分子量: 240.551
• InChiKey: OLMDDJRNCJFNOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-1,1,1-三乙氧基乙烷 、 2-amino-4-bromo-thiophenol; hydrochloride 以 乙醇 为溶剂， 以88%的产率得到2-氯甲基-5-溴苯并噻唑
  参考文献：
  名称：

  Mylari, Banavara L.; Scott, Pamela J.; Zembrowski, William J., Synthetic Communications, 1989, vol. 19, # 16, p. 2921 - 2924

  摘要：

  DOI：

文献信息

• Novel and Potent Aldose Reductase Inhibitors: 4-Benzyl- and 4-(Benzothiazol-2-ylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine-2-acetic Acid Derivatives.
  作者：Tomoji AOTSUKA、Hiroshi HOSONO、Toshio KURIHARA、Yoshiyuki NAKAMURA、Tetsuo MATSUI、Fujio KOBAYASHI

  DOI：10.1248/cpb.42.1264

  日期：——

  A number of 1, 4-benzothiazine-2-acetic acid derivatives (1, 2 and 3) and their bioisosteres (15b, 16, 18 and 20b) were synthesized and evaluated in vitro for the ability to inhibit aldose reductase (AR) in porcine lens. The compounds which exhibited potent activity in vitro were also assayed in vivo for inhibitory activity against sorbitol accumulation in the erythrocytes, sciatic nerve and lens of streptozotocin-diabetic rats. The 4-(substituted benzothiazol-2-ylmethyl)-1, 4-benzothiazine-2-acetic acid derivatives (2 and 3) showed more potent AR inhibitory activity than did the 4-(4-bromo-2-fluorobenzol)-1, 4-benzothiazine-2-acetic acid derivatives (1). 4-(4, 5, 7-Trifluorobenzothiazol-2-ylmethyl)-3, 4-dihydro-3-oxo-2H-1, 4-benzothiazine-2-acetic acid (2q, SPR-210) showed not only a potent AR-inhibitory activity in vitro (IC50 9.5×10-9 M) but also a significant reduction in sorbitol accumulation in rat sciatic nerve (ID50 0.1 mg/kg) and lens (ID50 9.8 mg/kg). Optical resolution of the racemic SPR-210 was achieved by means of a diastereomer salt method using (-)-brucine. The biological activities of both enantiomers, (+)- and (-)-SPR-210, were comparable to that of the racemate.

  合成了多种1,4-苯并噻唑-2-乙酸衍生物（1、2和3）及其生物等效物（15b、16、18和20b），并在体外评估其抑制猪眼晶状体醇糖还原酶（AR）的能力。在体外表现出强效活性的化合物，也在体内测定其对链脲菌素糖尿病大鼠的红细胞、坐骨神经和晶状体中甜菜糖积累的抑制活性。4-(取代苯并噻唑-2-亚甲基)-1,4-苯并噻唑-2-乙酸衍生物（2和3）比4-(4-溴-2-氟苯)-1,4-苯并噻唑-2-乙酸衍生物（1）显示出更强的AR抑制活性。4-(4,5,7-三氟苯并噻唑-2-亚甲基)-3,4-二氢-3-氧-2H-1,4-苯并噻唑-2-乙酸（2q, SPR-210）不仅在体外表现出强效的AR抑制活性（IC50 9.5×10^-9 M），而且在大鼠坐骨神经（ID50 0.1 mg/kg）和晶状体（ID50 9.8 mg/kg）中显著降低了甜菜糖的积累。通过使用(-)-布克因的互变异构盐方法实现了消旋体SPR-210的光学分解。两种对映体（+）-和(-)-SPR-210的生物活性与消旋体相当。
• 2-Phenylbanzothiazole polymers
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US04436886A1

  公开（公告）日：1984-03-13

  Mono- and di-acetylenic-substituted 2-phenylbenzothiazoles are thermally self-polymerized to form thermally stable polymers. The polymers are useful as laminating resins for fibrous composites, particularly for high temperature applications.

  单炔基和双炔基取代的2-苯基苯并噻唑可以热自聚形成热稳定性高的聚合物。这些聚合物可用作纤维复合材料的层压树脂，特别适用于高温应用。
• Di-acetylenyl-substituted 2-phenylbenzothiazoles
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US04442293A1

  公开（公告）日：1984-04-10

  Mono- and di-acetylenic-substituted 2-phenylbenzothiazoles are prepared by reacting the corresponding mono- or di-halogen-substituted 2-phenylbenzothiazole with an alkyne, such as 2-methyl-3-butyne-2-ol in the presence of a suitable catalyst.

  通过将相应的单卤素或双卤素取代的2-苯基苯并噻唑与炔烃反应（如2-甲基-3-丁炔-2-醇）在适当的催化剂存在下制备了单乙炔基和双乙炔基取代的2-苯基苯并噻唑。
• Preparation of ethynyl substituted 2-phenylbenzothiazoles
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US04559404A1

  公开（公告）日：1985-12-17

  Mono -and di-acetylenic-substituted 2-phenylbenzothiazoles are prepared by reacting the corresponding mono- or di-halogen-substituted 2-phenylbenzothiazole with an alkyne, such as 2-methyl-3-butyne-2-ol in the presence of a suitable catalyst.

  通过将相应的单卤代或双卤代2-苯基苯并噻唑与炔烃反应，如2-甲基-3-丁炔-2-醇，在适当的催化剂存在下制备单-和双乙炔基取代的2-苯基苯并噻唑。
• US4380619A
  申请人：——

  公开号：US4380619A

  公开（公告）日：1983-04-19