2-Chlormethyl-3,4-dihydro-3-(2-nitrophenyl)-4-chinazolinon | 80096-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-Chlormethyl-3,4-dihydro-3-(2-nitrophenyl)-4-chinazolinon
• 英文别名: 2-(chloromethyl)-3-(2-nitrophenyl)quinazolin-4-one
• CAS: 80096-22-6
• 化学式: C₁₅H₁₀ClN₃O₃
• 分子量: 315.716
• InChiKey: JCXMOHBBIZTNII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.03
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-Chlormethyl-3,4-dihydro-3-(2-nitrophenyl)-4-chinazolinon 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以78%的产率得到2-Azidomethyl-3,4-dihydro-3-(2-nitrophenyl)-4-chinazolinon
  参考文献：
  名称：

  Chinazolinone, 2. Mitt.: Synthese und einige Reaktionen von 2-Azidomethyl-3-aryl-4-chinazolinonen

  摘要：

  DOI：

  10.1007/bf00905474
• 作为产物：
  描述：

  邻氨基苯甲酸 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 2-Chlormethyl-3,4-dihydro-3-(2-nitrophenyl)-4-chinazolinon
  参考文献：
  名称：

  Synthesis and evaluation of quinazolin-4-ones as hypoxia-inducible factor-1α inhibitors

  摘要：

  Quinazolin-4-one 1 was identified as an inhibitor of the HIF-1 alpha transcriptional factor from a high-throughput screen. HIF-1 alpha up-regulation is common in many cancer cells. In this Letter, we describe an efficient one-pot sequential reaction for the synthesis of quinazolin-4-one 1 analogues. The structure-activity relationship (SAR) study led to the 5-fold more potent analogue, 16. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.07.043

文献信息

• Synthesis and screening of 2-(2-(4-substituted piperazine-1-yl)-5-phenylthiazol-4-yl)-3-aryl quinazolinone derivatives as anticancer agents
  作者：Ritesh N. Sharma、Rasik Ravani

  DOI：10.1007/s00044-012-0260-2

  日期：2013.6

  Synthesis of novel quinazolinone derivatives was performed from the reaction of N-benzoyl substituted piperazine-1-carbothioamide with 2-chloromethyl quinazolinone derivatives and screened for their in vitro cytotoxic activity by MTT assay. The cell lines used were NCI (human lung cancer cell), MCF 7 (Breast cancer cell), and HEK 293 (Normal epidermal kidney cell). Result of screening on cell line showed moderate to good anticancer activity for all the compounds. Compound 3d (IC50 = 1.1 +/- A 0.03 mu M) was found to be the most active compared to standard methotrexate (IC50 = 2.20 +/- A 0.18 mu M) and 5-florouracil (IC50 = 2.30 +/- A 0.49 mu M). Structure activity relationship of synthesized analogs suggested that the presence of NH linker with aryl moiety at the third position of quinazolinone ring was important for potent anticancer activity. Electron donating group on phenyl ring at the third position of quinazolinone ring gave better anticancer activity then unsubstituted phenyl and electron withdrawing group. Activity by substituted piperazine at 2nd position of thiazole linked with quinazolinone scaffold gave better activity in the order of H > CH3 > CO-C6H5. Our findings may impart new direction to medicinal chemists and biochemists for further investigations of quinazolinone-thiazole containing anticancer agents.
• Rao; Shankar Ch.; Reddy, Journal of the Indian Chemical Society, 1985, vol. 62, # 3, p. 234 - 237
  作者：Rao、Shankar Ch.、Reddy、Reddy

  DOI：——

  日期：——
• DOMANIG, R., MONATSH. CHEM., 1981, 112, N 10, 1195-1202
  作者：DOMANIG, R.

  DOI：——

  日期：——
• RAO, A. DEVENDER;SHANKAR, CH. RAVI;REDDY, P. BHAGHAVAN;REDDY, V. MALLA, J. INDIAN CHEM. SOC., 1985, 62, N 3, 234-237
  作者：RAO, A. DEVENDER、SHANKAR, CH. RAVI、REDDY, P. BHAGHAVAN、REDDY, V. MALLA

  DOI：——

  日期：——