3-(benzothiazol-2-ylthio)propionic acid azide | 199592-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(benzothiazol-2-ylthio)propionic acid azide
• 英文别名: 3-(1,3-Benzothiazol-2-ylsulfanyl)propanoyl azide
• CAS: 199592-96-6
• 化学式: C₁₀H₈N₄OS₂
• 分子量: 264.332
• InChiKey: DPOGQSLFTGLPRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(benzothiazol-2-ylthio)propionic acid azide 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 1-[2-(1,3-Benzothiazol-2-ylsulfanyl)ethyl]-3-methylurea
  参考文献：
  名称：

  Benzothiazole hydroxy ureas as inhibitors of 5-lipoxygenase: use of the hydroxyurea moiety as a replacement for hydroxamic acid

  摘要：

  A novel series of N-[(2-benzothiazolylthio)alkyl]-N'-hydroxyurea derivatives (9-25) was synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase both in vivo (mouse zymosan peritonitis assay) and in vitro (Ca2+ ionophore-stimulated human peripheral blood leukocyte model). The compounds of this series were based on the corresponding hydroxamic acid derivatives (1, 3, 4, and 5) which were moderately active in vitro but inactive in vivo. A number of compounds in the hydroxyurea series exhibited oral activity for 5-lipoxygenase inhibition. Results of studies relating structure to in vivo and in vitro 5-lipoxygenase activity are reported.

  DOI：

  10.1021/jm00095a012
• 作为产物：
  描述：

  3-(2-苯并噻唑硫代)丙酸 在 sodium azide 、 草酰氯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(benzothiazol-2-ylthio)propionic acid azide
  参考文献：
  名称：

  Benzothiazole hydroxy ureas as inhibitors of 5-lipoxygenase: use of the hydroxyurea moiety as a replacement for hydroxamic acid

  摘要：

  A novel series of N-[(2-benzothiazolylthio)alkyl]-N'-hydroxyurea derivatives (9-25) was synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase both in vivo (mouse zymosan peritonitis assay) and in vitro (Ca2+ ionophore-stimulated human peripheral blood leukocyte model). The compounds of this series were based on the corresponding hydroxamic acid derivatives (1, 3, 4, and 5) which were moderately active in vitro but inactive in vivo. A number of compounds in the hydroxyurea series exhibited oral activity for 5-lipoxygenase inhibition. Results of studies relating structure to in vivo and in vitro 5-lipoxygenase activity are reported.

  DOI：

  10.1021/jm00095a012

文献信息

• Anilide compounds, including use thereof in ACAT inhibitition
  申请人：Kowa Company, Ltd.

  公开号：US06204278B1

  公开（公告）日：2001-03-20

  The invention provides novel anilide compounds and pharmaceutical compositions comprising them. The invention relates to compounds of a formula: where Ar is an optionally-substituted aryl group; R4 and R5 are the same or different, and each is a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and R4 and R5 may together form a lower alkylene group of which one or more methylene moieties may optionally be substituted by oxygen and/or sulfur atoms; X is —NH—, or oxygen or sulfur atom; Y is —NH—, an oxygen or sulfur atom, or a sulfoxide or sulfone group; Z is a single bond, or —NH6—; R6 represents a hydrogen atom or a lower alkylene group; and n is an integer of from 0 to 15; and their salts and solvates. The compounds of the invention are useful as pharmaceutical compositions, especially as acyl coenzyme A cholesterol acyltransferase (ACAT) inhibitors.

  该发明提供了新型苯胺酰胺化合物及包含它们的药物组合物。该发明涉及具有以下结构的化合物：其中Ar是可选择取代的芳基；R4和R5相同或不同，每个都是氢原子、较低的烷基基团或较低的烷氧基团；R4和R5可以一起形成一个较低的烷基烯基，其中一个或多个亚甲基基团可以选择性地被氧和/或硫原子取代；X为—NH—，或氧或硫原子；Y为—NH—、氧或硫原子，或亚砜基或砜基；Z为单键，或—NH6—；R6代表氢原子或较低的烷基基团；n为0至15的整数；以及它们的盐和溶剂合物。该发明的化合物可用作药物组合物，特别是作为酰辅酶A胆固醇酰基转移酶（ACAT）抑制剂。
• Anilide compounds as ACAT inhibitors
  申请人：KOWA COMPANY LTD.

  公开号：EP0807627A2

  公开（公告）日：1997-11-19

  The invention provides novel anilide compounds and pharmaceutical compositions comprising them. The invention relates to compounds of a formula: where Ar is an optionally-substituted aryl group; R4 and R5 are the same or different, and each is a hydrogen atom, a lower alkyl group, or a lower alkoxy group; and R4 and R5 may together form a lower alkylene group of which one or more methylene moieties may optionally be substituted by oxygen and/or sulfur atoms; X is -NH-, or an oxygen or sulfur atom; Y is -NH-, an oxygen or sulfur atom, or a sulfoxide or sulfone group; Z is a single bond, or -NR6-; R6 represents a hydrogen atom or a lower alkylene group; and n is an integer of from 0 to 15; and their salts and solvates. The compounds of the invention are useful as pharmaceutical compositions, especially as acyl coenzyme A cholesterol acyltransferase (ACAT) inhibitors.

  本发明提供了新型苯胺化合物及其药物组合物。 本发明涉及式如下的化合物： 其中 Ar 是任选取代的芳基； R4 和 R5 相同或不同，且各自为氢原子、低级烷基或低级烷氧基；R4 和 R5 可共同形成低级亚烷基，其中一个或多个亚甲基可任选被氧原子和/或硫原子取代； X 是-NH-、氧原子或硫原子； Y 是-NH-、氧原子或硫原子、亚砜或砜基； Z 是单键，或 -NR6-； R6 代表氢原子或低级亚烷基；以及 n 是 0 至 15 的整数； 以及它们的盐和溶剂。 本发明的化合物可用作药物组合物，尤其是酰基辅酶 A 胆固醇酰基转移酶（ACAT）抑制剂。
• US6204278B1
  申请人：——

  公开号：US6204278B1

  公开（公告）日：2001-03-20
• Benzothiazole hydroxy ureas as inhibitors of 5-lipoxygenase: use of the hydroxyurea moiety as a replacement for hydroxamic acid
  作者：Michael N. Greco、William E. Hageman、Eugene T. Powell、Joseph J. Tighe、Francis J. Persico

  DOI：10.1021/jm00095a012

  日期：1992.8

  A novel series of N-[(2-benzothiazolylthio)alkyl]-N'-hydroxyurea derivatives (9-25) was synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase both in vivo (mouse zymosan peritonitis assay) and in vitro (Ca2+ ionophore-stimulated human peripheral blood leukocyte model). The compounds of this series were based on the corresponding hydroxamic acid derivatives (1, 3, 4, and 5) which were moderately active in vitro but inactive in vivo. A number of compounds in the hydroxyurea series exhibited oral activity for 5-lipoxygenase inhibition. Results of studies relating structure to in vivo and in vitro 5-lipoxygenase activity are reported.