2-amino-5-methoxy-benzenethiol; hydrochloride | 4274-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-5-methoxy-benzenethiol; hydrochloride
• 英文别名: 2-amino-5-methoxy-thiophenol; hydrochloride；5-Methoxy-2-aminobenzenethiol Hydrochloride；(4-Methoxy-2-sulfanylphenyl)azanium;chloride；(4-methoxy-2-sulfanylphenyl)azanium;chloride
• CAS: 4274-42-4
• 化学式: C₇H₉NOS*ClH
• mdl: MFCD17014608
• 分子量: 191.681
• InChiKey: CBEOFQYFYYBIED-UHFFFAOYSA-N

物化性质

• 熔点：
  210-211 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  36.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-methoxy-benzenethiol; hydrochloride 在 硒脲酸 、 溶剂黄146 作用下， 生成 6-Methoxybenzo-1,2,3-thiaselenazolium
  参考文献：
  名称：

  苯并1,2,3-硫代噻唑鎓盐的合成及某些性质

  摘要：

  DOI：

  10.1007/bf00945597

文献信息

• Therapeutic compounds
  申请人：——

  公开号：US20040102435A1

  公开（公告）日：2004-05-27

  Compounds of the formula (I) for use as an estrogen receptor-&bgr;-selective ligand are described wherein: X is O or S; and R 1 , R 3 R 6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  描述了用作雌激素受体β选择性配体的化合物的公式(I)，其中：X为O或S；R1，R3和R6如规范中所述。描述了这些化合物在治疗阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎和前列腺癌中的用途；以及制备它们的过程。
• 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。
• Therapeutic benzothiazole compounds
  申请人：Barlaam Bernard

  公开号：US20060111408A1

  公开（公告）日：2006-05-25

  Compounds of the formula (I) for use as an estrogen receptor -β-selective ligand are described wherein: X is O or S; and R 1 , R 3 -R 6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  本文描述了化学式（I）的化合物，可用作雌激素受体-β选择性配体，其中X为O或S；R1、R3-R6如规范中所述。描述了在治疗阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎和前列腺癌方面使用这些化合物的方法，以及制备它们的过程。
• ER-beta-selective ligands
  申请人：Barlaam Bernard

  公开号：US20070208066A1

  公开（公告）日：2007-09-06

  Compounds of the formula (I) for use as an estrogen receptor -β-selective ligand are described wherein: X is O or S; and R 1 , R 3 -R 6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  本文描述了化学式（I）的化合物，用作雌激素受体-β选择性配体，其中X为O或S；R1，R3-R6如规范所述。描述了在治疗阿尔茨海默病，焦虑症，抑郁症，骨质疏松症，心血管疾病，类风湿性关节炎和前列腺癌方面使用这些化合物的方法，以及制造它们的过程。
• Therapeutic benzoxazole compounds
  申请人：AstraZeneca AB

  公开号：US07045539B2

  公开（公告）日：2006-05-16

  Compounds of the formula (I) for use as an estrogen receptor-β-selective ligand are described wherein: X is O or S; and R1, R3 R6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  本发明描述了化学式（I）的化合物，用作雌激素受体-β选择性配体，其中：X为O或S；R1、R3、R6如说明书中所述。本发明还描述了这些化合物在治疗阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎和前列腺癌中的应用，以及制备它们的过程。