1,2,3,4-tetrahydroazepino<3,2,1-kl>phenothiazin-3-one | 69513-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1,2,3,4-tetrahydroazepino<3,2,1-kl>phenothiazin-3-one
• 英文别名: 1,2,3,4-Tetrahydroazepino-<3,2,1-he>-phenothiazin-3-on；1,2-dihydro-4H-azepino[3,2,1-kl]phenothiazin-3-one；17-Thia-10-azatetracyclo[8.7.1.05,18.011,16]octadeca-1,3,5(18),11,13,15-hexaen-7-one
• CAS: 69513-40-2
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: HQQRQABJUKHQKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydroazepino<3,2,1-kl>phenothiazin-3-one 、 二甲胺 在 molecular sieve 、 sodium cyanoborohydride 作用下， 生成 3-(dimethylamino)-1,2,3,4-tetrahydroazepino<3,2,1-kl>phenothiazine
  参考文献：
  名称：

  Conformationally restricted phenothiazine neuroleptics. 1. 3-(Dimethylamino)-1,2,3,4-tetrahydroazepino[3,2,1-kl]phenothiazine

  摘要：

  A rigid analogue of promazine, 3-(dimethylamino)-1,2,3,4-tetrahydroazepino[3,2,1-kl]phenothiazine (1), was prepared by reductive amination of the corresponding ketone 4. An X-ray crystallographic study revealed that the seven-membered ring of the hydrochloride salt of 1 exists as a half-chair-like form with the dimethylammonium group in an equatorial-like conformation. Compound 1 was approximately one-half as active as promazine as an inhibitor of [3H]spiperone binding in rat corpus striatal homogenates. In homogenates obtained from calf caudate tissue, however, 1 was only about one-twentieth as active as promazine as an inhibitor of [3H] spiperone binding. As a stimulator of homovanilic acid (HVA) synthesis in rat corpus striatum in vivo, it was about one-tenth as active as promazine.

  DOI：

  10.1021/jm00182a022
• 作为产物：
  描述：

  1,2-dihydro-3H-pyrido[3,2,1-kl]phenothiazin-3-one 在 吡啶 、 lithium perchlorate 、 calcium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 1,2,3,4-tetrahydroazepino<3,2,1-kl>phenothiazin-3-one
  参考文献：
  名称：

  Kim,S.M.; Martin,A.R., Journal of Heterocyclic Chemistry, 1978, vol. 15, p. 1507 - 1508

  摘要：

  DOI：

文献信息

• MARTIN A. R.; KIM S. H.; YAMAMURA H. I.; HORN A. S., J. MED. CHEM., 1980, 23, NO 8, 938-941
  作者：MARTIN A. R.、 KIM S. H.、 YAMAMURA H. I.、 HORN A. S.

  DOI：——

  日期：——
• KIM S. H.; MARTIN A. R., J. HETEROCYCL. CHEM., 1978, 15, NO 8, 1507-1508
  作者：KIM S. H.、 MARTIN A. R.

  DOI：——

  日期：——
• Kim,S.M.; Martin,A.R., Journal of Heterocyclic Chemistry, 1978, vol. 15, p. 1507 - 1508
  作者：Kim,S.M.、Martin,A.R.

  DOI：——

  日期：——
• Conformationally restricted phenothiazine neuroleptics. 1. 3-(Dimethylamino)-1,2,3,4-tetrahydroazepino[3,2,1-kl]phenothiazine
  作者：Arnold R. Martin、Sun H. Kim、Henry I. Yamamura、Alan S. Horn

  DOI：10.1021/jm00182a022

  日期：1980.8

  A rigid analogue of promazine, 3-(dimethylamino)-1,2,3,4-tetrahydroazepino[3,2,1-kl]phenothiazine (1), was prepared by reductive amination of the corresponding ketone 4. An X-ray crystallographic study revealed that the seven-membered ring of the hydrochloride salt of 1 exists as a half-chair-like form with the dimethylammonium group in an equatorial-like conformation. Compound 1 was approximately one-half as active as promazine as an inhibitor of [3H]spiperone binding in rat corpus striatal homogenates. In homogenates obtained from calf caudate tissue, however, 1 was only about one-twentieth as active as promazine as an inhibitor of [3H] spiperone binding. As a stimulator of homovanilic acid (HVA) synthesis in rat corpus striatum in vivo, it was about one-tenth as active as promazine.