7-(Benzylthio)-8-nitro-1,2,3,4-tetrahydroisoquinoline Hydrochloride | 78104-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 7-(Benzylthio)-8-nitro-1,2,3,4-tetrahydroisoquinoline Hydrochloride
• 英文别名: 7-Benzylthio-8-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride；7-benzylsulfanyl-8-nitro-1,2,3,4-tetrahydroisoquinoline;hydrochloride
• CAS: 78104-33-3
• 化学式: C₁₆H₁₆N₂O₂S*ClH
• 分子量: 336.842
• InChiKey: OUQORWSECPBUEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(Benzylthio)-8-nitro-1,2,3,4-tetrahydroisoquinoline Hydrochloride 在 ammonium hydroxide 、 sodium acetate 、 乙酸酐 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 2-Acetyl-7-(benzylthio)-8-nitro-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Inhibiting phenylethanolamine N-methyltransferase with thiadiazolo and

  摘要：

  Thiadiazolo-和oxadiazolotetrahydroisoquinoline化合物是苯乙醇胺N-甲基转移酶的抑制剂。

  公开号：

  US04258049A1
• 作为产物：
  描述：

  7-chloro-8-nitro-isoquinoline 在 盐酸 、 氢氧化钾 、 硼烷四氢呋喃络合物 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 7.5h， 生成 7-(Benzylthio)-8-nitro-1,2,3,4-tetrahydroisoquinoline Hydrochloride
  参考文献：
  名称：

  Tetrahydro thiadiazolo isoquinolines: synthesis and inhibition of phenylethanolamine-N-methyltransferase

  摘要：

  A series of 7,8-fused heterocyclic tetrahydroisoquinolines were synthesized and tested as inhibitors of rabbit adrenal phenylethanolamine-N-methyltransferase (PNMT). 6,7,8,9-Tetrahydro[1,2,3]thiadiazolo[5,4-h]isoquinoline 5 (SK&F 86607) was found to be a potent inhibitor of PNMT with an IC50 similar to that of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline (1, SK&F 64139). The isomeric tetrahydro[1,2,3]thiadiazolo[4,5-h]- and tetrahydro[1,2,5]thiadiazolo[3,4-h]isoquinolines, 13 and 20, were also potent PNMT inhibitors. However, substitution of Cl at position 5 (17) resulted in loss of potency similar to the loss observed in the 5-chloro analogue of 1. The 1,2,5 isomer 20 showed only a small drop in activity at 10(-6) M. All of the thiadiazoles were more potent than the 7,8-benzo-fused analogue 36. Fusion of other five-membered heterocyclic ring systems at the 7,8-position, e.g. triazole 22 and imidazoles 24 and 26, resulted in a decrease of PNMT inhibition. The alpha-adrenoreceptor affinities of 1 and 5 were also compared.

  DOI：

  10.1021/jm00127a027

文献信息

• Inhibiting phenylethanolamine N-methyltransferase with thiadiazolo and
  申请人：SmithKline Corporation

  公开号：US04258049A1

  公开（公告）日：1981-03-24

  Thiadiazolo- and oxadiazolotetrahydroisoquinoline compounds are inhibitors of phenylethanolamine N-methyltransferase.

  Thiadiazolo-和oxadiazolotetrahydroisoquinoline化合物是苯乙醇胺N-甲基转移酶的抑制剂。
• Tetrahydroisoquinoline derivatives, process for preparing them and compositions containing them
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0023761A1

  公开（公告）日：1981-02-11

  Thiadiazolo- and oxadiazolo-tetrahydroisoquinoline derivatives which are inhibitors of phenylethanolamine N-methyltransferase which catalyzes the final step in the biosynthesis of epinephrine. The compounds of the invention can be prepared by various methods, and in general they will be administered as pharmaceutical compositions.

  噻二唑和噁二唑四氢异喹啉衍生物是苯乙醇胺 N-甲基转移酶的抑制剂，该酶催化肾上腺素生物合成的最后一步。本发明的化合物可以通过各种方法制备，一般来说，它们将作为药物组合物给药。
• Method of producing alpha2 antagonism
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0074741B1

  公开（公告）日：1986-11-12
• US4258049A
  申请人：——

  公开号：US4258049A

  公开（公告）日：1981-03-24
• US4352809A
  申请人：——

  公开号：US4352809A

  公开（公告）日：1982-10-05