2-hydrazino-3-(3-chlorophenyl)quinazoline-4(3H)-one | 66679-73-0

• 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-hydrazino-3-(3-chlorophenyl)quinazoline-4(3H)-one
• 英文别名: 3-(3-chloro-phenyl)-2-hydrazino-3H-quinazolin-4-one；3-(3-Chlorophenyl)-2-hydrazinylquinazolin-4-one
• CAS: 66679-73-0
• 化学式: C₁₄H₁₁ClN₄O
• 分子量: 286.721
• InChiKey: NHZAKSRENKMJBB-UHFFFAOYSA-N

物化性质

• 熔点：
  222 °C
• 沸点：
  492.1±47.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydrazino-3-(3-chlorophenyl)quinazoline-4(3H)-one 、 丁二酸二乙酯 反应 5.0h， 以32%的产率得到3-[4-(3-Chloro-phenyl)-5-oxo-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-1-yl]-propionic acid ethyl ester
  参考文献：
  名称：

  Kottke; Kuhmstedt; Knoke, Pharmazie, 1983, vol. 38, # 1, p. 25 - 28

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(3-氯苯基)-2-疏基-3H-喹唑啉-4-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 以82%的产率得到2-hydrazino-3-(3-chlorophenyl)quinazoline-4(3H)-one
  参考文献：
  名称：

  氰化合溴化物和乙酰乙酸乙酯在杂环中的应用：3-芳基喹唑啉酮四环衍生物的新型合成

  摘要：

  在这项工作中，三环1-氨基-4-（取代的苯基） - [1,2,4]三唑并[4,3一]喹唑啉-5（4 ħ） -酮3用处理2-肼基3的合成-（取代的苯基）喹唑啉-4（3 H）-one 2与溴化氰一起用乙酰乙酸乙酯将其环化，得到目标稠合的喹唑啉-4（3H）one 4稠合四环衍生物。合成的化合物已使用IR和1 H NMR，质谱数据以及元素分析进行了表征。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.440

文献信息

• Synthesis and Anticonvulsant Activity Evaluation of 4-Phenyl-[1,2,4]triazolo[4,3-<i>a</i>]quinazolin-5(4<i>H</i>)-one and Its Derivatives
  作者：Hong-Jian Zhang、Peng Jin、Shi-Ben Wang、Fu-Nan Li、Li-Ping Guan、Zhe-Shan Quan

  DOI：10.1002/ardp.201500115

  日期：2015.8

  A series of 4‐(substituted‐phenyl)‐[1,2,4]triazolo[4,3‐a]quinazolin‐5(4H)‐ones (6a–x) with triazole and other heterocyclic substituents (7–14) were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity by maximal electroshock (MES) and rotarod neurotoxicity tests. Among the compounds studied, 6o and 6q showed wide margins of safety with protective indices

  一系列具有三唑和其他杂环取代基 (7-14) 的 4-(取代-苯基)-[1,2,4] 三唑并 [4,3-a] 喹唑啉-5(4H)-酮 (6a-x)合成了化合物，并通过最大电休克 (MES) 和旋转棒神经毒性试验评估了化合物的抗惊厥活性和神经毒性。在研究的化合物中，6o 和 6q 显示出广泛的安全范围，其保护指数 (PI) 远高于目前使用的药物（PI6o > 25.5，PI6q > 26.0）。化合物 6o 和 6q 对 MES 诱导的小鼠癫痫发作显示出显着的口服活性，ED50 值分别为 88.02 和 94.6 mg/kg。还发现这两种化合物对由戊四唑和荷包牡丹碱诱发的癫痫发作具有强效活性。
• Cynogen bromide and ethylacetoacetate in heterocyclization: Novel synthesis of tetracyclic derivative of 3-aryl quinazolinones
  作者：M. B. Deshmukh、Suresh S. Patil、Sanjeevani S. Patil、Swati D. Jadhav

  DOI：10.1002/jhet.440

  日期：——

  ne 3 was synthesized by treatment of 2‐hydrazinyl‐3‐(substituted phenyl)quinazolin‐4(3H)‐one 2 with cyanogen bromide, which on cyclization with ethylacetoacetate to get the targeted fused tetracyclic derivatives of quinazoli‐4(3H)one 4. The synthesized compounds have been characterized using IR and 1H NMR, mass spectral data together with elemental analysis. J. Heterocyclic Chem., (2010).

  在这项工作中，三环1-氨基-4-（取代的苯基） - [1,2,4]三唑并[4,3一]喹唑啉-5（4 ħ） -酮3用处理2-肼基3的合成-（取代的苯基）喹唑啉-4（3 H）-one 2与溴化氰一起用乙酰乙酸乙酯将其环化，得到目标稠合的喹唑啉-4（3H）one 4稠合四环衍生物。合成的化合物已使用IR和1 H NMR，质谱数据以及元素分析进行了表征。J.杂环化​​学。（2010）。
• Novel Nonpeptide CCK-B Antagonists:  Design and Development of Quinazolinone Derivatives as Potent, Selective, and Orally Active CCK-B Antagonists
  作者：Janak K. Padia、Mark Field、Joanna Hinton、Ken Meecham、Julius Pablo、Rob Pinnock、Bruce D. Roth、Lakhbir Singh、Nirmala Suman-Chauhan、Bharat K. Trivedi、Louise Webdale

  DOI：10.1021/jm970373j

  日期：1998.3.1

  We have designed a novel series of CCK-B receptor antagonists by combining key pharmacophores, an arylurea moiety of 1 and a quinazolinone ring of 3, from two known series. Our earlier studies showed that compounds with methylene linkers in our "target" produced moderate binding affinity and selectivity for CCK-B receptors, whereas its higher and lower homologues resulted in loss of affinity. Introduction of -NH- as a linker dramatically enhanced binding affinity and selectivity for CCK-B receptors, thus providing several compounds with single-digit nanomolar binding affinity and excellent selectivity. Analogous to the earlier studies of the series of quinazolinone derivatives 3, we also found 3-isopropoxyphenyl as a preferred substitution on the N-3 quinazolinone. Electron-withdrawing substitutions on the urea terminal phenyl ring enhanced the CCK-B potency. Representative compounds of this series were tested in the functional assay and showed pure antagonist profiles. Compounds 51 and 61 were orally active in the elevated rat X-maze test. These compounds were also evaluated for their pharmacokinetic profile. The absolute oral bioavailability of compound 61 was 22% in rats.
• KOTTKE K.;KUEHMSTEDT H.;KNOKE D,, PHAMAZIE, 1983, 38, NO 1, 25-28
  作者：KOTTKE K.、KUEHMSTEDT H.、KNOKE D,

  DOI：——

  日期：——
• KOTTKE K.; KUEHMSTEDT H., PHARMAZIE, 1978, 33, NO 1, 19-23
  作者：KOTTKE K.、 KUEHMSTEDT H.

  DOI：——

  日期：——