2-phenyl-3-(4-benzoyl hydrazide)-1,3-quinazolin-4(4H)-one | 148321-04-4

• 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-phenyl-3-(4-benzoyl hydrazide)-1,3-quinazolin-4(4H)-one
• 英文别名: 4-(4-oxo-2-phenylquinazolin-3(4H)-yl)benzohydrazide；4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate hydrazide；4-(2-phenyl-4-oxo-(3H)-quinazolin-3-yl)benzoic acid hydrazide；4-[4-oxoquinazolin-2-phenyl-3(4H)-yl]-N-benzoylhydrazide；4-(4-oxo-2-phenylquinazolin-3-yl)benzohydrazide
• CAS: 148321-04-4
• 化学式: C₂₁H₁₆N₄O₂
• 分子量: 356.384
• InChiKey: MFHYGDLOERSGIF-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C(Solv: methanol (67-56-1))
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-(4-benzoyl hydrazide)-1,3-quinazolin-4(4H)-one 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2-(2-chloro-5-nitrophenyl)-3-[4-(4-oxo-2-phenylquinazolin-3(4H)-yl)benzoyl]-1,3,4-thiadiazolium-5-thiolate
  参考文献：
  名称：

  Synthesis, characterization, and antimicrobial studies of novel 1,3,4-thiadiazolium-5-thiolates

  摘要：

  Sixteen novel thiadiazolium derivatives 6(a-h) and 12(a-h) were synthesized by conventional route starting from anthranilic acid using different acid chloride derivatives. The structure of all the newly synthesized compounds was established by IR, NMR, mass spectroscopy, and elemental analysis. The compounds were also screened for their antibacterial activity against some important bacterial species. Some of the compounds were found excellent active against these species.

  DOI：

  10.1007/s00044-011-9632-2
• 作为产物：
  描述：

  methyl 4-(2-phenyl-4-oxo-(3H)-quinazolin-3-yl)benzoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到2-phenyl-3-(4-benzoyl hydrazide)-1,3-quinazolin-4(4H)-one
  参考文献：
  名称：

  新型 5-amino-4-cyano-1H-pyrazole 和 quinazolin-4(3H)-one 衍生物的合成和抗菌活性

  摘要：

  由酸酰肼 (3) 和相应的醛或醛糖合成了新的取代芳酰腙 (4a-f)。5-氨基-4-氰基-1H-吡唑衍生物（6a-f）是通过芳酰基腙（4a-f）与丙二腈的反应制备的。测试合成的化合物对各种细菌和真菌的抗菌活性，并显示出中度至高度的抑制活性。在其结构中包含糖部分和吡唑环的化合物显示出最高的抗微生物活性。

  DOI：

  10.1007/s12272-010-1202-5

文献信息

• Novel Cationic Quinazolin-4(3<i>H</i>)-one Conjugated Fullerene Nanoparticles as Antimycobacterial and Antimicrobial Agents
  作者：Manishkumar B. Patel、Uma Harikrishnan、Nikunj N. Valand、Nishith R. Modi、Shobhana K. Menon

  DOI：10.1002/ardp.201200371

  日期：2013.3

  bearing a substituted‐quinazolin‐4(3H)‐one moiety as a side arm were synthesized using the 1,3‐dipolar cycloaddition reaction of C60 with azomethine ylides generated from the corresponding Schiff bases of substituted quinazolinones. The synthesized compounds 5a–f were characterized by elemental analysis, FT‐IR, 1H NMR, 13C NMR, and ESI‐MS and screened for their antibacterial activity against Mycobacterium

  使用 C60 与由取代喹唑啉酮的相应席夫碱产生的偶氮甲碱叶立德的 1,3-偶极环加成反应合成了一系列带有取代喹唑啉-4(3H)-one 部分作为侧臂的新型阳离子富勒烯衍生物。合成的化合物 5a-f 通过元素分析、FT-IR、1H NMR、13C NMR 和 ESI-MS 进行表征，并筛选了它们对结核分枝杆菌 (H37RV) 的抗菌活性和对选定的革兰氏阳性菌（金黄色葡萄球菌和金黄色葡萄球菌）的抗菌活性。化脓性链球菌）和革兰氏阴性菌（铜绿假单胞菌、肺炎克雷伯菌和大肠杆菌）细菌和真菌菌株（白色念珠菌、棒状曲霉和黑曲霉）分别。所有化合物都表现出显着的活性，
• Heterocyclic synthesis: A convenient route to some 2-mercepto 1,3,4-oxadiazole and green chemistry microwave-induced one-pot synthesis of 2-aryl 1,3,4-oxadiazole in quinazolone and their antibacterial and antifungal activity
  作者：A. R. Desai、K. R. Desai

  DOI：10.1002/jhet.5570420539

  日期：2005.7

  6-substi-tuted-3-[4-(5-phenyl-1,3,4-oxadiazol-2-yl) phenyl]-2-substitutedquinazolin-4(3H)-one 3(a-l) were synthesized using conventional and microwave techniques respectively and were screened for antibacterial and antifungal activity.

  几个6-取代的-3-[（（5-巯基-1,3,4-恶二唑-2-基）甲基] -2-取代的喹唑啉-4（3 H）-一个或6-取代的-3- [4- （5-mercepto-1,3,4-oxadiazol-2-yl）phenyl] -2-取代的quinazolin-4（3 H）-一个2（al）和6-取代的-3-[（5-phenyl-1， 3,4-恶二唑-2-基）甲基] -2-取代的喹唑啉-4（3 H）-一或6-取代的-3- [4-（5-苯基-1,3,4-恶二唑-2分别使用常规技术和微波技术合成了（基）苯基] -2-取代的喹唑啉-4（3 H）-1 3（al），并对其抗菌和抗真菌活性进行了筛选。
• Synthesis and antimicrobial activity of novel 5-amino-4-cyano-1H-pyrazole and quinazolin-4(3H)-one derivatives
  作者：Mohamed T. Abdel-Aal、Abdel-Aleem H. Abdel-Aleem、Laila I. Ibahim、Ahmed L. Zein

  DOI：10.1007/s12272-010-1202-5

  日期：2010.12

  New substituted aroylhydrazones (4a-f) were synthesized from the acid hydrazide (3) and the corresponding aldehyde or aldose. 5-Amino-4-cyano-1H-pyrazole derivatives (6a-f) were prepared by the reaction of the aroylhydrazones (4a-f) with malononitrile. The synthesized compounds were tested for antimicrobial activity against various bacteria and fungi and showed moderate to high inhibition activities

  由酸酰肼 (3) 和相应的醛或醛糖合成了新的取代芳酰腙 (4a-f)。5-氨基-4-氰基-1H-吡唑衍生物（6a-f）是通过芳酰基腙（4a-f）与丙二腈的反应制备的。测试合成的化合物对各种细菌和真菌的抗菌活性，并显示出中度至高度的抑制活性。在其结构中包含糖部分和吡唑环的化合物显示出最高的抗微生物活性。
• Synthesis, characterization and biological activity of new 3(4H)-quinazolinone derivatives
  作者：A. I. El-Shenawy

  DOI：10.1134/s1070363217090237

  日期：2017.9

  synthesis of many heterocyclic systems. Ethyl 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate 2 upon reaction with hydrazine hydrate gave 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate benzoylhydrazide 3. Compound 3 on treatment with 3-nitrobenzaldehyde, acetyl acetone, ethyl acetoacetate, and ammonium thiocyanate yielded compounds 4–8, respectively. Isothiocyanate 8 was used for the synthesis of other

  喹唑啉基苯甲酸1被用作许多杂环系统合成的前体。与水合肼反应后的4- [4-氧代-2-苯基喹唑啉-3（4 H）-基]苯甲酸乙酯2得到4- [4-氧代-2-苯基喹唑啉-3（4 H）-基]苯甲酸乙酯苯甲酰肼3。化合物3治疗与3-硝基苯甲醛，乙酰丙酮，乙酰乙酸乙酯，和硫氰酸铵，得到化合物4 - 8，分别。异硫氰酸盐8用于合成其他喹唑啉衍生物9 – 16通过与各种试剂的反应。所有新合成的喹唑啉酮衍生物均已通过1 H NMR，IR和质谱表征。对大多数合成产品的抗菌和抗真菌活性进行了评估，其中一些具有高活性。
• Synthesis and anticonvulsant activity of novel quinazolin-4(3H)-one derived pyrazole analogs
  作者：Veerachamy Alagarsamy、Govindaraj Saravanan

  DOI：10.1007/s00044-012-0169-9

  日期：2013.4

  Eighteen novel 6,8-(dibromo/unsubstituted)-2-(methyl/phenyl)-3-(4-(5-(substitutedphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl)phenyl)-quinazolin-4(3H)-ones 4a-4r were designed and synthesized in good yield. Antiepileptic screening of the title compounds was performed using MES and scPTZ seizures tests while the neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 4d, 4e, 4p, 4q, and 4r were found active in MES model, while 4a, 4d, 4f, 4m, and 4p showed significant antiepileptic activity in scPTZ model. Further, all these eight compounds were administered to rats and compounds 4e, 4p, and 4q showed better activity than Phenytoin in oral route. Among these compounds 4p revealed protection in MES after i.p. administration at a dose of 30 mg/kg (0.5 h) and 100 mg/kg (4 h). The compound 4p also provided protection in the scPTZ at a dose of 100 mg/kg (0.5 h) and 300 mg/kg (4 h).