4-naphthalen-1-yl-9-naphthalen-1-ylmethylene-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamine | 1322199-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-naphthalen-1-yl-9-naphthalen-1-ylmethylene-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamine
• 英文别名: 4-naphthalen-1-yl-9-(naphthalen-1-ylmethylidene)-5,6,7,8-tetrahydrocyclohepta[d]pyrimidin-2-amine
• CAS: 1322199-65-4
• 化学式: C₃₀H₂₅N₃
• 分子量: 427.549
• InChiKey: BTFJAXDRMDTZCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.8
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-萘甲醛 、 环庚酮 在 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-naphthalen-1-yl-9-naphthalen-1-ylmethylene-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamine
  参考文献：
  名称：

  Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents

  摘要：

  An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydroquinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H(37)Rv strain and the a-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 mu g/mL against M. tuberculosis and very good inhibition of a-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 mu g/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.040

文献信息

• Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents
  作者：Nimisha Singh、Sarvesh Kumar Pandey、Namrata Anand、Richa Dwivedi、Shyam Singh、Sudhir Kumar Sinha、Vinita Chaturvedi、Natasa Jaiswal、Arvind Kumar Srivastava、Priyanka Shah、M. Imran Siddiqui、Rama Pati Tripathi

  DOI：10.1016/j.bmcl.2011.06.040

  日期：2011.8

  An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydroquinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H(37)Rv strain and the a-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 mu g/mL against M. tuberculosis and very good inhibition of a-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 mu g/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.