2-氯[1,3]噻唑并[4,5-h]异喹啉 | 35317-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 2-氯[1,3]噻唑并[4,5-h]异喹啉
• 英文名称: 2-Chlorothiazolo<4,5-h>isochinolin
• 英文别名: 2-chloro-thiazolo[4,5-h]isoquinoline；2-Chlorothiazolo[4,5-h]isoquinoline；2-chloro-[1,3]thiazolo[4,5-h]isoquinoline
• CAS: 35317-81-8
• 化学式: C₁₀H₅ClN₂S
• 分子量: 220.682
• InChiKey: IORGSQCYQBFZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-氯[1,3]噻唑并[4,5-h]异喹啉 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以70%的产率得到2-氯-6,7,8,9-四氢[1,3]噻唑并[4,5-h]异喹啉
  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
• 作为产物：
  描述：

  7-氨基异喹啉 生成 2-氯[1,3]噻唑并[4,5-h]异喹啉
  参考文献：
  名称：

  噻唑异喹啉。四、噻唑并[4,5-h]-和噻唑并[5,4-f]异喹啉的合成和光谱。一些取代异喹啉的紫外和质子磁共振谱

  摘要：

  由7-氨基异喹啉分四步合成噻唑并[4,5-h]异喹啉：与硫氰酸钾和溴反应生成7-氨基-8-硫氰异喹啉；后者用盐酸环化生成2-氨基噻唑并[4,5-h]异喹啉，然后Sandmeyer反应生成2-氯衍生物，最后用氢碘酸和磷还原。噻唑并[5,4-f]异喹啉由6-氨基异喹啉通过6-氨基-5-硫氰异喹啉制备。2,5-二氨基噻唑并[5,4-h]异喹啉的合成是通过将5-氨基异喹啉得到的5-乙酰氨基-8-氨基异喹啉环化而实现的。在 5-amino-8-thiocyano- 和 8-amino-5-thiocyanoisoquinolines 中，硫氰基用 8N 盐酸和乙醇 (1:1) 水解成硫醇基。 uv 和 pmr

  DOI：

  10.1139/v71-674

文献信息

• GIRARD, GERALD R.;BONDINELL, WILLIAM E.;HILLEGASS, LEONARD M.;HOLDEN, KEN+, J. MED. CHEM. , 32,(1989) N, C. 1566-1571
  作者：GIRARD, GERALD R.、BONDINELL, WILLIAM E.、HILLEGASS, LEONARD M.、HOLDEN, KEN+

  DOI：——

  日期：——
• Tetrahydro thiadiazolo isoquinolines: synthesis and inhibition of phenylethanolamine-N-methyltransferase
  作者：Gerald R. Girard、William E. Bondinell、Leonard M. Hillegass、Kenneth G. Holden、Robert G. Pendleton、Irene Uzinskas

  DOI：10.1021/jm00127a027

  日期：1989.7

  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.
• Thiazoloisoquinolines. IV. The Synthesis and Spectra of Thiazolo[4,5-<i>h</i>]- and Thiazolo[5,4-<i>f</i>]isoquinolines. The Ultraviolet and Proton Magnetic Resonance Spectra of Some Substituted Isoquinolines
  作者：Alfred Taurins、Richard Kang-Chuan Hsia

  DOI：10.1139/v71-674

  日期：1971.12.15

  5-amino-8-thiocyano- and 8-amino-5-thiocyanoisoquinolines, the thiocyano group was hydrolyzed to the thiol group with 8 N hydrochloric acid and ethanol (1:1).The u.v. and p.m.r. spectra of the intermediate isoquinolines, and the i.r., u.v., and n.m.r. spectra of thiazoloisoquinolines were studied.

  由7-氨基异喹啉分四步合成噻唑并[4,5-h]异喹啉：与硫氰酸钾和溴反应生成7-氨基-8-硫氰异喹啉；后者用盐酸环化生成2-氨基噻唑并[4,5-h]异喹啉，然后Sandmeyer反应生成2-氯衍生物，最后用氢碘酸和磷还原。噻唑并[5,4-f]异喹啉由6-氨基异喹啉通过6-氨基-5-硫氰异喹啉制备。2,5-二氨基噻唑并[5,4-h]异喹啉的合成是通过将5-氨基异喹啉得到的5-乙酰氨基-8-氨基异喹啉环化而实现的。在 5-amino-8-thiocyano- 和 8-amino-5-thiocyanoisoquinolines 中，硫氰基用 8N 盐酸和乙醇 (1:1) 水解成硫醇基。 uv 和 pmr