methyl 10H-phenothiazine-1-carboxylate | 4063-33-6

• 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: methyl 10H-phenothiazine-1-carboxylate
• 英文别名: methyl 1-phenothiazinecarboxylate；1-carbomethoxyphenothiazine；1-Methoxycarbonyl-phenthiazin；Phenthiazin-carbonsaeure-(4)-methylester；10H-phenothiazine-1-carboxylic acid methyl ester；phenothiazine-1-carboxylic acid methyl ester；Phenothiazin-1-carbonsaeure-methylester；1-Carbomethoxyphenothiazin
• CAS: 4063-33-6
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: GZHAPWRJGXSDSL-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  448.0±34.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934300000

反应信息

• 作为反应物：
  描述：

  methyl 10H-phenothiazine-1-carboxylate 在 乙醇 、 肼 作用下， 生成 phenothiazine-1-carboxylic acid hydrazide
  参考文献：
  名称：

  SOME DERIVATIVES OF PHENOTHIAZINE. II.¹

  摘要：

  DOI：

  10.1021/jo01376a020
• 作为产物：
  描述：

  1,2-dihydropyrrolo[3,2,1-kl]-phenothiazin-1,2-dione 在 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 3.0h， 生成 methyl 10H-phenothiazine-1-carboxylate
  参考文献：
  名称：

  New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives

  摘要：

  In this work, we reported the synthesis and evaluation of the analgesic, antiinflammatory, and antiplatelet properties of new phenothiazine-attached acylhydrazone derivatives (6), designed exploring the molecular hybridization approach between antipsychotic chlorpromazine (4) and other heterocyclic derivatives (3) and (5) developed at LASSBio. Target compounds were synthesized in very good yields exploiting diphenylamine (7) as starting material, through regioselective functionalization of the C-1 position of 10H-phenothiazine ring. The evaluation of platelet antiaggregating profile lead us to identify a new potent prototype of antiplatelet derivative, that is (6a) (IC50 = 2.3 muM), which acts in arachidonic acid pathway probably by inhibition of platelet COX-1 enzyme. Additionally, the change of para-substituent group of acylhydrazone framework permitted us to identify hydrophilic carboxylate derivative (6g) and hydrophobic bromo derivative (66) as two new leads of analgesics more active than dipyrone used as standard and with selective peripheral or central mechanism of action. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.009

文献信息

• Cyclohepta[<i>b</i>][1,4]benzothiazines and Their Diazine Analogues. 1. Formation and Reactions of Cyclohepta[<i>b</i>][1,4]benzothiazines
  作者：Kimio Shindo、Sumio Ishikawa、Tetsuo Nozoe

  DOI：10.1246/bcsj.58.165

  日期：1985.1

  title benzothiazine (9). Although 9 was stable under basic conditions, its N-methyl cation reversibly afforded the ring-opened 2-[o-(methylamino)phenylthio]tropone in alkali. Oxidation of 9 with hydrogen peroxide in methanol underwent a rearrangement reaction to afford (exclusively) phenothiazine and its 1-formyl derivative. A similar H2O2 oxidation of 10-methoxycyclohepta[b][1,4]benzothiazine gave

  2-Chlorotropone 与邻氨基苯硫醇反应得到 2-(o-氨基苯硫基)tropone，它很容易在稀甲醇 HCl 中环化得到标题苯并噻嗪 (9)。虽然 9 在碱性条件下是稳定的，但它的 N-甲基阳离子在碱中可逆地提供开环的 2-[o-(甲氨基)苯硫基]tropone。在甲醇中用过氧化氢氧化 9 进行重排反应以提供（仅）吩噻嗪及其 1-甲酰基衍生物。10-甲氧基环庚烷[b][1,4]苯并噻嗪的类似H2O2氧化主要产生甲基吩噻嗪-1-羧酸酯和3-甲酰基-1-甲氧基吩噻嗪。用过氧化氢进一步氧化这些产物，产生它们的 S-氧化物和 S,S-二氧化物。这些环庚苯并噻嗪的反应性将与 O- 和 N- 类似物的反应性联系起来讨论。
• Cauquil,G. et al., Bulletin de la Societe Chimique de France, 1960, p. 1049 - 1066
  作者：Cauquil,G. et al.

  DOI：——

  日期：——
• The Metalation of Phenothiazine¹
  作者：Henry Gilman、David A. Shirley、Paul R. Van Ess

  DOI：10.1021/ja01232a035

  日期：1944.4
• Synthesis of N-methyl-1,9-ethenophenothiazine, a briged syn-metacyclophane
  作者：V. Boekelheide、Richard A. Hollins

  DOI：10.1021/jo00816a012

  日期：1971.8
• Driscoll,J.S.; Nealey,R.H., Journal of Heterocyclic Chemistry, 1965, vol. 2, p. 272 - 275
  作者：Driscoll,J.S.、Nealey,R.H.

  DOI：——

  日期：——