2-(2-氯苯并[d]噻唑-6-基)乙酸 | 152149-00-3

• 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-(2-氯苯并[d]噻唑-6-基)乙酸
• 英文名称: 2-(2-Chlorobenzo[d]thiazol-6-yl)acetic acid
• 英文别名: 2-(2-chloro-1,3-benzothiazol-6-yl)acetic acid
• CAS: 152149-00-3
• 化学式: C₉H₆ClNO₂S
• 分子量: 227.671
• InChiKey: HBDVBZKFZBCJEW-UHFFFAOYSA-N

物化性质

• 沸点：
  400.4±20.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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-(2-氯苯并[d]噻唑-6-基)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 N-[2-(2-Chlorobenzothiazol-6-yl)ethyl]-N-[(R)-(+)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]-N-methylamine
  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：

  对氨基苯乙酸 在 盐酸 、 甲酸 、 溴 、 溶剂黄146 、 copper(l) chloride 、 sodium nitrite 作用下， 反应 4.67h， 生成 2-(2-氯苯并[d]噻唑-6-基)乙酸
  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

文献信息

• Bicyclic heteroaromatic derivatives for the treatment of immune and inflammatory disorders
  申请人：——

  公开号：US20030171413A1

  公开（公告）日：2003-09-11

  Compounds of formula (1) are described, wherein q is zero or the integer 1, 2 or 3; R which when present may be attached to any available carbon or nitrogen atom of the bicyclic heteroaromatic ring of formula (1) is an atom or group -L 3 (Alk 3 ) w L 4 (R 8 ) u ; X is an O atom or a S(O) m atom or group in which m is zero or the integer 1 or 2 or an NR group; Y is a N atom or a CR 1a group in which R 1a is a group R or a group R 1 ; R 1 which may he on any available carbon atom of the bicyclic heteroaromatic ring of formula (1) is a hydrogen atom or a group -Alk 1 L 1 CyAlk 2 L 2 D; provided that at least one but not both of R 1 and R 1a is the group -Alk 1 L 1 CyAlk 2 L 2 D. The compounds are potent inhibitors of the interaction between CCR-3 and it chemokine ligands and are of use in the prophylaxis and treatment of immune or inflammatory disorders in which inhibition of this interaction can have a beneficial effect.

  描述了式（1）的化合物，其中q为零或整数1、2或3；R，当存在时，可以连接到式（1）的双环杂芳环的任何可用碳或氮原子上，是一个原子或基团-L3(Alk3)wL4(R8)u；X为一个O原子或S(O)matom或基团，在其中m为零或整数1或2或一个NR基团；Y为一个N原子或CR1agroup，在其中R1a是一个基团R或一个基团R1；R1，可以位于式（1）的双环杂芳环的任何可用碳原子上，是一个氢原子或一个基团-Alk1L1CyAlk2L2D；但要求R1和R1a中至少一个而不是两者都是基团-Alk1L1CyAlk2L2D。这些化合物是CCR-3与其趋化因子配体之间相互作用的有效抑制剂，可用于预防和治疗通过抑制该相互作用可能产生有益效果的免疫或炎症性疾病。
• TRIAZOLOPYRIDAZINE PROTEIN KINASE MODULATORS
  申请人：Smith Christopher Ronald

  公开号：US20100120739A1

  公开（公告）日：2010-05-13

  The present disclosure relates to triazolopyridazine protein kinase modulators of Formula (I), methods of using these compounds to treat diseases mediated by kinase activity.

  本公开涉及式(I)的三唑并吡嗪蛋白激酶调节剂，以及使用这些化合物治疗由激酶活性介导的疾病的方法。
• BICYCLIC HETEROAROMATIC DERIVATIVES FOR THE TREATMENT OF IMMUNE AND INFLAMMATORY DISORDERS
  申请人：Celltech R&D Limited

  公开号：EP1311502A1

  公开（公告）日：2003-05-21
• US5288749A
  申请人：——

  公开号：US5288749A

  公开（公告）日：1994-02-22
• US8071581B2
  申请人：——

  公开号：US8071581B2

  公开（公告）日：2011-12-06