4-phenyl-9H-pyrimido[4,5-b]indole | 524047-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-phenyl-9H-pyrimido[4,5-b]indole
• CAS: 524047-81-2
• 化学式: C₁₆H₁₁N₃
• 分子量: 245.283
• InChiKey: GZIWKYWVOALFHX-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C(Solv: benzene (71-43-2))
• 沸点：
  496.6±25.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-9H-pyrimido[4,5-b]indole 、 碘甲烷 在 sodium ethanolate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以48%的产率得到9-methyl-4-phenylpyrimido[4,5-b]indole
  参考文献：
  名称：

  4-苯基-9H-嘧啶并[4,5-b]吲哚的2-硫代衍生物的合成

  摘要：

  3-亚苄基-2-乙氧基吲哚啉四氟硼酸盐与硫脲反应生成 4-苯基嘧啶并[4,5-b]吲哚-2(1H)-硫酮、其 3,4-二氢衍生物和相应的二硫化物的混合物，产物比例取决于反应条件。描述了所得化合物的许多转化，特别是那些产生 2-烷硫基嘧啶并吲哚衍生物的转化。

  DOI：

  10.1007/s11172-006-0379-8
• 作为产物：
  描述：

  2-oxo-4-phenylpyrimido<4,5-b>indole 在 一水合肼 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 23.0h， 生成 4-phenyl-9H-pyrimido[4,5-b]indole
  参考文献：
  名称：

  摘要：

  A method was developed for the synthesis of 2-oxo-4-phenyl-2,3-dihydro-9H-pyrimido[4,5-b]indole as well as of 2-chloro- and 2-nitramino-4-phenylpyrimido[4,5-b]indoles. The replacement of the chlorine atom in 2-chloropyrimidoindole gave rise to a number of its functional derivatives (morpholino, azido, and cyano). The reaction of 2-chloro-substituted pyrimidoindole with hydrazine hydrate and catalytic hydrogenation of 2-nitraminopyrimidoindole were studied.

  DOI：

  10.1023/a:1021688616234

文献信息

• [EN] 4-PHENYL-PYRIMIDO [4,5-B] INDOLE DERIVATIVES<br/>[FR] DERIVES 4-PHENYL-PYRIMIDO [4,5-B]INDOLES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004058764A1

  公开（公告）日：2004-07-15

  The present invention relates to 4-phenyl-pyrimido[4,5-b]indoles which are useful as an active ingredient of pharmaceutical preparations. The 4-phenyl-pyrimido[4,5-b]indoles of the present invention have MKK7 and MKK4 inhibitory activity, and can be used for the prophylaxis and treatment of diseases associated with MKK7 and MKK4 activity.Such diseases include, inflammatory and immunoregulatory disorders and diseases such as asthma, atopic dermatitis, rhinitis, allergic rhinitis, allergic diseases, COPD, septic shock, arthritis, joint diseases and myocardial injuries, as well as autoimmune pathologies such as rheumatoid arthritis, Grave's disease, and atherosclerosis as well as cancer.The compounds of the present invention are also useful for treatment of ischemia, myocardial injury, pulmonary hypertension, renal failure, Huntington's chorea and cardiac hypertrophy, as well as neurodegenerative disorders such as Parkinson's disease, Alzheimer's disease and focal ischemia.

  本发明涉及4-苯基-吡咯并[4,5-b]吲哚，它们可用作药物制剂的活性成分。本发明的4-苯基-吡咯并[4,5-b]吲哚具有MKK7和MKK4的抑制活性，可用于预防和治疗与MKK7和MKK4活性相关的疾病。这些疾病包括炎症和免疫调节紊乱疾病，如哮喘、特应性皮炎、鼻炎、过敏性鼻炎、过敏性疾病、慢性阻塞性肺病、脓毒性休克、关节炎、关节疾病和心肌损伤，以及风湿性关节炎、格氏病和动脉粥样硬化等自身免疫病理病变，还可用于缺血、心肌损伤、肺动脉高压、肾功能衰竭、亨廷顿舞蹈症和心脏肥大的治疗，以及帕金森病、阿尔茨海默病和局灶性缺血等神经退行性疾病。
• ——
  作者：V. P. Borovik、O. P. Shkurko

  DOI：10.1023/a:1021688616234

  日期：——

  A method was developed for the synthesis of 2-oxo-4-phenyl-2,3-dihydro-9H-pyrimido[4,5-b]indole as well as of 2-chloro- and 2-nitramino-4-phenylpyrimido[4,5-b]indoles. The replacement of the chlorine atom in 2-chloropyrimidoindole gave rise to a number of its functional derivatives (morpholino, azido, and cyano). The reaction of 2-chloro-substituted pyrimidoindole with hydrazine hydrate and catalytic hydrogenation of 2-nitraminopyrimidoindole were studied.
• Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole
  作者：V. P. Borovik、V. G. Vasil’ev、O. P. Shkurko

  DOI：10.1007/s11172-006-0379-8

  日期：2006.6

  The reaction of 3-benzylidene-2-ethoxyindolenine tetrafluoroborate with thiourea gives a mixture of 4-phenylpyrimido[4,5-b]indole-2(1H)-thione, its 3,4-dihydro derivative, and the corresponding disulfide, the product ratio depending on the reaction conditions. A number of transformations of the resulting compounds, in particular, those giving 2-alkylthio pyrimidoindole derivatives are described.

  3-亚苄基-2-乙氧基吲哚啉四氟硼酸盐与硫脲反应生成 4-苯基嘧啶并[4,5-b]吲哚-2(1H)-硫酮、其 3,4-二氢衍生物和相应的二硫化物的混合物，产物比例取决于反应条件。描述了所得化合物的许多转化，特别是那些产生 2-烷硫基嘧啶并吲哚衍生物的转化。