2-甲基-6-苯并噻唑乙酸 | 103261-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-甲基-6-苯并噻唑乙酸
• 英文名称: 2-methylbenzothiazole-6-acetic acid
• 英文别名: (2-methyl-benzothiazol-6-yl)-acetic acid；2-(2-methyl-1,3-benzothiazol-6-yl)acetic acid
• CAS: 103261-69-4
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: QLEXVRBMZIBOTR-UHFFFAOYSA-N

物化性质

• 熔点：
  203.5 °C
• 沸点：
  389.1±17.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-6-苯并噻唑乙酸 在 硼烷四氢呋喃络合物 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 ((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-[2-(2-methyl-benzothiazol-6-yl)-ethyl]-amine
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m
• 作为产物：
  描述：

  6-(氯甲基)-2-甲基-1,3-苯并噻唑 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 2-甲基-6-苯并噻唑乙酸
  参考文献：
  名称：

  Zubarovskii,V.M.; Khodot,G.P., Journal of general chemistry of the USSR, 1960, vol. 30, p. 1268 - 1272

  摘要：

  DOI：

文献信息

• ATTEMPT TOWARDS SYN-BENZOTHIAZOLOPHANE: SYNTHESIS AND CONFORMATIONAL STUDY OF SYN-DITHIA-[3.3](2,6) BENZOTHIAZOLOPHANE
  作者：Sabir Η Mashraqui、Sukeerthi Kumar、Kishore R. Nivalkar

  DOI：10.1515/hc.2001.7.1.73

  日期：2001.1
• Discovery and SAR of 2-aminothiazole inhibitors of cyclin-dependent kinase 5/p25 as a potential treatment for Alzheimer’s disease
  作者：Christopher J. Helal、Mark A. Sanner、Christopher B. Cooper、Thomas Gant、Mavis Adam、John C. Lucas、Zhijun Kang、Stanley Kupchinsky、Michael K. Ahlijanian、Bonnie Tate、Frank S. Menniti、Kristin Kelly、Marcia Peterson

  DOI：10.1016/j.bmcl.2004.09.006

  日期：2004.11

  High-throughput screening with cyclin-dependent kinase 5 (cdk5)/p25 led to the discovery of N-(5-isopropyl-thiazol-2-yl)isobutyramide (1). This compound is an equipotent inhibitor of cdk5 and cyclin-dependent kinase 2 (cdk2)/cyclin E (IC50 = ca. 320nM). Parallel and directed synthesis techniques were utilized to explore the SAR of this series. Up to 60-fold improvements in potency at cdk5 and 12-fold selectivity over cdk2 were achieved. (C) 2004 Elsevier Ltd. All rights reserved.
• Structure−Activity Studies for a Novel Series of <i>N</i>-(Arylethyl)-<i>N</i>-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-<i>N</i>-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities
  作者：Michael D. Meyer、Arthur A. Hancock、Karin Tietje、Kevin B. Sippy、Rajnandan Prasad、David M. Stout、David L. Arendsen、B. Greg Donner、William A. Carroll

  DOI：10.1021/jm960723m

  日期：1997.3.1

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.
• Zubarovskii,V.M.; Khodot,G.P., Journal of general chemistry of the USSR, 1960, vol. 30, p. 1268 - 1272
  作者：Zubarovskii,V.M.、Khodot,G.P.

  DOI：——

  日期：——