2-methyl-2,3-dihydro-1H,10H-phenothiazin-4-one | 57750-46-6

• 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: 2-methyl-2,3-dihydro-1H,10H-phenothiazin-4-one
• 英文别名: 2-Methyl-2,3-dihydro-1H-phenothiazin-4[10H]-one；2-Methyl-2,3-dihydro-1H-phenothiazin-4(10H)-one；2-methyl-1,2,3,10-tetrahydrophenothiazin-4-one
• CAS: 57750-46-6
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: NCESZJDHEIYVMB-UHFFFAOYSA-N

物化性质

• 熔点：
  266-268 °C (decomp)
• 沸点：
  362.2±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲基-3-羟基环己-2-烯酮 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 生成 2-methyl-2,3-dihydro-1H,10H-phenothiazin-4-one
  参考文献：
  名称：

  Synthesis, characterization, and anticonvulsant activity of enaminones. Part 5: Investigations on 3-carboalkoxy-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-one derivatives

  摘要：

  A new series of anticonvulsant 3-carboalkoxy-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-ones is herein reported. 2-Aminothiophenols underwent cyclocondensation with 4-carboalkoxy-5-methylcyclohexane-1,3-diones in refluxing dimethylsulfoxide (DMSO) to yield 3-carboalkoxy-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-ones, 4a-k. In the case of the carbo-tert-butoxy derivatives (4c and 4k) prolonged reaction times led to the isolation of the respective 3-unsubstituted-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-ones (41 and 4m) instead. Significant anticonvulsant activity was displayed by these analogues, most particularly 4k, which was active at 30 mg/kg intraperitoneally tip) in mice in the maximal electroshock seizure (MES) evaluation, with no toxicity noted at dosages up to 300 mg/kg. Oral (po) rat evaluation of 4k in the MES evaluation provided an ED50 Of 17.60 mg/kg, with no toxicity noted at dosages up to 500 mg/kg, providing a protective index (PI = TD50/ED50) > 28.40. These compounds represent the first reported series of phenothiazines which possess anticonvulsant activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80009-6

文献信息

• 3-carboalkoxy-2, 3-dihydro-1H-phenothiazin-4[10H]-one derivatives
  申请人：Howard University

  公开号：US05994349A1

  公开（公告）日：1999-11-30

  Phenothiazines of the formula: ##STR1## where R.sub.1 is H or --COOR, where R is selected from the group consisting of branched or unbranched alkyl groups containing from 1 to 4 carbon atoms, and where X is selected from H, branched or unbranched alkyl groups containing from 1 to 4 carbons, and halogen, and pharmaceutically acceptable salts thereof. Particularly preferred phenothiazines are those wherein X is hydrogen, chloro, bromo or methyl, R.sub.1 is COOR, and R is methyl, ethyl or t-butyl.

  式子为：##STR1##的苯并噻唑类化合物，其中R.sub.1为H或--COOR，其中R为从含有1到4个碳原子的支链或非支链烷基组成的组，并且X为H、含有1到4个碳原子的支链或非支链烷基、卤素，以及其药学上可接受的盐。特别喜欢的苯并噻唑类化合物是，其中X为氢、氯、溴或甲基，R.sub.1为COOR，R为甲基、乙基或叔丁基。
• A Facile Synthesis of 2,3-Dihydro-1<i>H</i>-phenothiazin-4(10<i>H</i>)-ones
  作者：M. L. Jain、R. P. Soni

  DOI：10.1055/s-1983-30578

  日期：——
• Miyano,S. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1146 - 1149
  作者：Miyano,S. et al.

  DOI：——

  日期：——
• JAIN, M. L.;SONI, R. P., SYNTHESIS, BRD, 1983, N 11, 933-935
  作者：JAIN, M. L.、SONI, R. P.

  DOI：——

  日期：——
• MIYANO S.; ABE N.; SUMOTO K., J. CHEM. SOC. CHEM. COMMUNS <CCOM-A8>, 1975, NO 18, 760
  作者：MIYANO S.、 ABE N.、 SUMOTO K.

  DOI：——

  日期：——