6-Chloro-2-methyl-3-(5-methyl-1,2-oxazol-3-yl)quinazolin-4-one | 250588-22-8

• 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: 6-Chloro-2-methyl-3-(5-methyl-1,2-oxazol-3-yl)quinazolin-4-one
• CAS: 250588-22-8
• 化学式: C₁₃H₁₀ClN₃O₂
• 分子量: 275.694
• InChiKey: YHFCPXLHWCGZCR-UHFFFAOYSA-N

物化性质

• 沸点：
  489.5±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻甲氧基苯甲醛 、 6-Chloro-2-methyl-3-(5-methyl-1,2-oxazol-3-yl)quinazolin-4-one 在 溶剂黄146 作用下， 反应 12.0h， 以73%的产率得到6-Chloro-2-[(E)-2-(2-methoxy-phenyl)-vinyl]-3-(5-methyl-isoxazol-3-yl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis and antileukemic activity of new 3-(5-methylisoxazol-3-yl) and 3-(pyrimidin-2-yl)-2-styrylquinazolin-4(3H)-ones

  摘要：

  3-(3-Methylisoxazol-5-yl) and 3-(pyrimidin-2-yl)-2-styrylquinazolin-4(3H)-ones 8a-l and 9a,c-e,h-l were synthesized by refluxing in acetic acid the corresponding 2-methylquinazolinones 6 and 8 with the opportune benzoic aldehyde for 12 h. The synthesized styrylquinazolinones 8a-l and 9a,c-e,h-l were tested in vitro for their antileukemic activity against L-1210 (murine leukemia), K-562 (human chronic myelogenous leukemia) and HL-60 (human leukemia) cell lines showing in some cases good activity.

  DOI：

  10.1016/j.farmac.2003.10.006
• 作为产物：
  描述：

  5-氯-2-硝基苯甲酰氯 在 盐酸 、 氢氧化钾 、 三乙胺 、 tin(ll) chloride 作用下， 反应 9.0h， 生成 6-Chloro-2-methyl-3-(5-methyl-1,2-oxazol-3-yl)quinazolin-4-one
  参考文献：
  名称：

  新型3-(Isoxazol-3-yl)-quinazolin-4 (3H)-one衍生物的合成及药理活性

  摘要：

  合成了几种新的 3-(isoxazol-3-yl)-quinazolin-4 (3H)-one 衍生物，并测试了它们的镇痛和抗炎活性，以及​​它们的急性毒性和致溃疡作用。在扭体和醋酸腹膜炎试验中，一些化合物的活性与保泰松一样。它们的致溃疡作用非常低。

  DOI：

  10.1002/(sici)1521-4184(19993)332:2<50::aid-ardp50>3.0.co;2-s

文献信息

• Synthesis, cytotoxicity, and inhibitory effects on tubulin polymerization of a new 3-heterocyclo substituted 2-styrylquinazolinones
  作者：Demetrio Raffa、Michael C. Edler、Giuseppe Daidone、Benedetta Maggio、Mourad Merickech、Salvatore Plescia、Domenico Schillaci、Ruoli Bai、Ernest Hamel

  DOI：10.1016/j.ejmech.2003.12.009

  日期：2004.4

  In order to study the influence of 3-substitution on the cytotoxic activity of 2-styrylquinazolinones, new 6-chloro-2-styryl-3-(heteroaryl)-4(3H)-quinazolinones were synthesized by refluxing equimolar amounts of 6-chloro-2-methyl-3-(heteroaryl)-4(3H)-quinazolinones and benzaldehyde in glacial acetic acid. At 1 mug ml(-1) concentration, almost all 2-styrylquinazolinones showed some cytotoxic activity against the L1210 and K562 leukemia cell lines. However, only 6-chloro-2-styryl-3-(pyrimidin-2yl)-4(3H)-quinazolinone inhibited the growth of these cells by over 50%. This last compound was also the only member of the series that inhibited tubulin polymerization, with air IC50 value of 5.8 versus 3.2 muM for colchicine. It was also examined for effects on the growth of human MCF7 breast carcinoma cells and Burkitt lymphoma CA46 cells, which had IC50 values of 0.34 and 1.0 muM, respectively. At 10 muM 6-chloro-2-styryl-3-(pyrimidin-2yl)-4(3H)-quinazolinone induced G2/M arrest (66%) in Burkitt cells, with a mitotic index of 20%. At 3.4 muM, it caused disruption of the cellular microtubule system of the MCF7 cells. Both these cellular effects are consistent with its mechanism of action resulting from its inhibitory effect on tubulin assembly. (C) 2004 Elsevier SAS. All rights reserved.
• Synthesis and Pharmacological Activities of Novel 3-(Isoxazol-3-yl)-quinazolin-4(3H)-one Derivatives
  作者：Giuseppe Daidone、Demetrio Raffa、Benedetta Maggio、Fabiana Plescia、Vincenza Maria Catena Cutuli、Nunzio Guido Mangano、Antonina Caruso

  DOI：10.1002/(sici)1521-4184(19993)332:2<50::aid-ardp50>3.0.co;2-s

  日期：1999.3

  Several new 3‐(isoxazol‐3‐yl)‐quinazolin‐4(3H)‐one derivatives were synthesized and tested for their analgesic and antiinflammatory activities, as well as for their acute toxicity and ulcerogenic effect. A few compounds were as active as phenylbutazone in the writhing and acetic acid peritonitis tests. They had a very low ulcerogenic effect.

  合成了几种新的 3-(isoxazol-3-yl)-quinazolin-4 (3H)-one 衍生物，并测试了它们的镇痛和抗炎活性，以及​​它们的急性毒性和致溃疡作用。在扭体和醋酸腹膜炎试验中，一些化合物的活性与保泰松一样。它们的致溃疡作用非常低。
• Synthesis and antileukemic activity of new 3-(5-methylisoxazol-3-yl) and 3-(pyrimidin-2-yl)-2-styrylquinazolin-4(3H)-ones
  作者：Demetrio Raffa、Giuseppe Daidone、Benedetta Maggio、Stella Cascioferro、Fabiana Plescia、Domenico Schillaci

  DOI：10.1016/j.farmac.2003.10.006

  日期：2004.6

  3-(3-Methylisoxazol-5-yl) and 3-(pyrimidin-2-yl)-2-styrylquinazolin-4(3H)-ones 8a-l and 9a,c-e,h-l were synthesized by refluxing in acetic acid the corresponding 2-methylquinazolinones 6 and 8 with the opportune benzoic aldehyde for 12 h. The synthesized styrylquinazolinones 8a-l and 9a,c-e,h-l were tested in vitro for their antileukemic activity against L-1210 (murine leukemia), K-562 (human chronic myelogenous leukemia) and HL-60 (human leukemia) cell lines showing in some cases good activity.