N-(3-acetylphenyl)-3-chlorobenzamide | 196408-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-acetylphenyl)-3-chlorobenzamide
• CAS: 196408-42-1
• 化学式: C₁₅H₁₂ClNO₂
• mdl: MFCD00095786
• 分子量: 273.719
• InChiKey: MNGHLXFZVLRJAW-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  361.1±27.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-甲醛-9-甲基咔唑 、 N-(3-acetylphenyl)-3-chlorobenzamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.17h， 以85%的产率得到3-chloro-N-[3-[(E)-3-(9-methylcarbazol-3-yl)prop-2-enoyl]phenyl]benzamide
  参考文献：
  名称：

  作为黄嘌呤氧化酶和酪氨酸酶抑制剂的N- {3- [3-（9-甲基-9 H-咔唑-3-基）-丙烯酰基]-苯基}-苯甲酰胺/酰胺衍生物的合成，生物学评估和分子对接

  摘要：

  3-甲酰基-9-甲基咔唑与3-氨基苯乙酮的各种酰胺的Claisen-Schmidt缩合反应得到N- {3- [3-（3-（9-甲基-9 H-咔唑-3-基）-丙烯酰基]-丙烯基]苯基}-苯甲酰胺/酰胺衍生物。研究了所有化合物的体外黄嘌呤氧化酶（XO），酪氨酸酶和黑色素生成抑制活性。大多数目标化合物具有比标准药物更强的XO抑制活性（IC 50  = 4.3–5.6μM）。有趣的是，发现带有环丙基环的化合物7q是最有效的XO抑制剂（IC 50  = 4.3μM）。分子建模研究深入了解了其与XO的结合模式。化合物7a，7d，7e，7克和7K被发现是酪氨酸酶的强效抑制剂（IC 50  = 14.01-17.52μM）。这些结果表明这些化合物可能用于设计和开发新型XO和酪氨酸酶抑制剂。

  DOI：

  10.1016/j.bmc.2012.07.001
• 作为产物：
  描述：

  间氨基苯乙酮 、 3-氯苯甲酰氯 在 sodium hydroxide 作用下， 生成 N-(3-acetylphenyl)-3-chlorobenzamide
  参考文献：
  名称：

  作为黄嘌呤氧化酶和酪氨酸酶抑制剂的N- {3- [3-（9-甲基-9 H-咔唑-3-基）-丙烯酰基]-苯基}-苯甲酰胺/酰胺衍生物的合成，生物学评估和分子对接

  摘要：

  3-甲酰基-9-甲基咔唑与3-氨基苯乙酮的各种酰胺的Claisen-Schmidt缩合反应得到N- {3- [3-（3-（9-甲基-9 H-咔唑-3-基）-丙烯酰基]-丙烯基]苯基}-苯甲酰胺/酰胺衍生物。研究了所有化合物的体外黄嘌呤氧化酶（XO），酪氨酸酶和黑色素生成抑制活性。大多数目标化合物具有比标准药物更强的XO抑制活性（IC 50  = 4.3–5.6μM）。有趣的是，发现带有环丙基环的化合物7q是最有效的XO抑制剂（IC 50  = 4.3μM）。分子建模研究深入了解了其与XO的结合模式。化合物7a，7d，7e，7克和7K被发现是酪氨酸酶的强效抑制剂（IC 50  = 14.01-17.52μM）。这些结果表明这些化合物可能用于设计和开发新型XO和酪氨酸酶抑制剂。

  DOI：

  10.1016/j.bmc.2012.07.001

文献信息

• Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure–activity relationship analysis, and biological activity
  作者：Hongcai Li、Chao Wang、Tino Sanchez、Yanmei Tan、Chunying Jiang、Nouri Neamati、Guisen Zhao

  DOI：10.1016/j.bmc.2009.01.077

  日期：2009.4

  HIV-1 integrase, which catalyzes the integration of the viral genome into the cellular chromosome, is an essential enzyme for retroviral replication, and represents an attractive and validated target in the development of therapeutics against AIDS. In this paper, 17 amide-containing novel diketoacids were designed and synthesized, and their ability to inhibit HIV-1 integrase was tested. The structure-activity relationships were also analyzed. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of novel curcumin analogues as anti-inflammatory, anti-cancer and anti-oxidant agents
  作者：Babasaheb P. Bandgar、Baliram S. Hote、Shivkumar S. Jalde、Rajesh N. Gacche

  DOI：10.1007/s00044-011-9834-7

  日期：2012.10

  A series of novel curcumin analogues 5a-m were synthesized by Claisen-Schmidt condensation of various aromatic and heteroaromatic amides of 3-aminoactophenones 4a-m with 3-bromo-2,4,6-trimethoxybenzaldehyde and characterized by IR, H-1 NMR and mass spectroscopic analysis and were evaluated for anti-inflammatory, anti-cancer and anti-oxidant activity. Out of the 13 synthesized compounds, compounds 5f, 5j and 5m were excellent inhibitors of TNF-alpha and IL-6. Compounds 5c, 5e, 5b and 5d showed potent COX-2 inhibition, compounds 5d and 5f have shown good trypsin inhibition and compounds 5e, 5g and 5c exhibited excellent beta-glucuronidase inhibition. Compounds 5l and 5m showed potent anti-cancer activity against selected five human cancer cell lines. All the compounds exhibited moderate free radical scavenging activity, while compounds 5a and 5m were excellent OH radical scavengers.
• Synthesis and antioxidant, cytotoxicity and antimicrobial activities of novel curcumin mimics
  作者：Babasaheb P. Bandgar、Shivkumar S. Jalde、Balaji L. Korbad、Sachin A. Patil、Hemant V. Chavan、Santosh N. Kinkar、Laxman K. Adsul、Sadanand N. Shringare、Shivraj H. Nile

  DOI：10.3109/14756366.2011.587416

  日期：2012.4.1

  Claisen-Schmidt condensation of 3-(1,2,3,6-tetrahydro-1-methylpyridin-4-yl)-2,4,5-trimethoxybenzaldehyde 3 and various aromatic, heterocyclic and alicyclic amides of 3- aminoacetophenone 6(a-s) afforded novel curcumin mimics. All the synthesized compounds were characterized by IR, H-1 NMR, Mass spectroscopy and evaluated for antioxidant, cytotoxicity and antimicrobial activity. Out of the 20 compounds screened, compounds 7i, 7l, 7q, and 7n have shown excellent radical scavenging activity, compounds 7o, 7t, 7f, and 7r have shown significant xanthine oxidase inhibition, and compounds 7a, 7k and 7l were found to be potent inhibitors of selected cancer cell lines. Compounds 7h, 7t, 7l, 7i, and 7e have shown good antibacterial activity, whereas compounds 7j, 7f, 7o, 7h, and 7t exhibited significant antifungal activity.
• Synthesis, biological evaluation, and molecular docking of N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives as xanthine oxidase and tyrosinase inhibitors
  作者：Babasaheb P. Bandgar、Laxman K. Adsul、Hemant V. Chavan、Sadanand N. Shringare、Balaji L. Korbad、Shivkumar S. Jalde、Shrikant V. Lonikar、Shivraj H. Nile、Amol L. Shirfule

  DOI：10.1016/j.bmc.2012.07.001

  日期：2012.9

  their in vitro xanthine oxidase (XO), tyrosinase and melanin production inhibitory activity. Most of the target compounds had more potent XO inhibitory activity than the standard drug (IC50 = 4.3–5.6 μM). Interestingly, compound 7q bearing cyclopropyl ring was found to be the most potent inhibitor of XO (IC50 = 4.3 μM). Molecular modelling study gave an insight into its binding modes with XO. Compounds

  3-甲酰基-9-甲基咔唑与3-氨基苯乙酮的各种酰胺的Claisen-Schmidt缩合反应得到N- 3- [3-（3-（9-甲基-9 H-咔唑-3-基）-丙烯酰基]-丙烯基]苯基}-苯甲酰胺/酰胺衍生物。研究了所有化合物的体外黄嘌呤氧化酶（XO），酪氨酸酶和黑色素生成抑制活性。大多数目标化合物具有比标准药物更强的XO抑制活性（IC 50  = 4.3–5.6μM）。有趣的是，发现带有环丙基环的化合物7q是最有效的XO抑制剂（IC 50  = 4.3μM）。分子建模研究深入了解了其与XO的结合模式。化合物7a，7d，7e，7克和7K被发现是酪氨酸酶的强效抑制剂（IC 50  = 14.01-17.52μM）。这些结果表明这些化合物可能用于设计和开发新型XO和酪氨酸酶抑制剂。