N-Benzoyl-anthranilsaeure-p-toluidid | 94871-76-8

• 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-Benzoyl-anthranilsaeure-p-toluidid
• 英文别名: 2-benzamido-N-(4-methylphenyl)benzamide
• CAS: 94871-76-8
• 化学式: C₂₁H₁₈N₂O₂
• mdl: MFCD00378021
• 分子量: 330.386
• InChiKey: VEAAJCAQUORQBA-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  385.5±35.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzoyl-anthranilsaeure-p-toluidid 在 六甲基二硅氮烷 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以73 mg的产率得到3-(4-甲基苯基)-2-苯基喹唑啉-4-酮
  参考文献：
  名称：

  Synthesis of 3-Substituted and 2,3-Disubstituted Quinazolinones via Cu-Catalyzed Aryl Amidation

  摘要：

  Cul/4-hydroxy-L-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 degrees C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.

  DOI：

  10.1021/ol300084v
• 作为产物：
  描述：

  2-(苯甲酰基氨基)苯甲酸 在 H3[PW12O40]*13H2O 作用下， 以 neat (no solvent) 为溶剂， 反应 0.35h， 生成 N-Benzoyl-anthranilsaeure-p-toluidid
  参考文献：
  名称：

  可回收的 Keggin 杂多酸作为一种环境友好的催化剂，用于在无溶剂条件下微波辐射下合成新的 2-苯甲酰氨基-N-苯基-苯甲酰胺衍生物和生物活性评价

  摘要：

  2-苯甲酰氨基-N-苯基-苯甲酰胺衍生物 (5a-h) 由 2-苯基-3,1-(4H)-苯并恶嗪-4-one 3 和取代的苯胺 4a-h 在 Keggin 型存在下制备杂多酸系列（H3PW12O40·13H2O；H4SiW12O40·13H2O；H4SiMo12O40·13H2O；和H3PMo12O40·13H2O）作为催化剂，无溶剂和微波辐射。我们发现使用H3PW12O40·13H2O酸与微波辐射耦合可以在短时间内获得高产率反应。化合物结构由1H-NMR和13C-NMR确定。合成化合物的抗菌和抗真菌活性表现出抑制细菌和真菌的生长。

  DOI：

  10.3390/molecules23010008

文献信息

• Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives: Search for anticancer agent
  作者：Malleshappa N. Noolvi、Harun M. Patel、Varun Bhardwaj、Ankit Chauhan

  DOI：10.1016/j.ejmech.2011.03.015

  日期：2011.6

  The synthesis of some 2-furano-4(3H)-quinazolinones, diamides (open ring quinazolines), quinoxalines and their biological evaluation as antitumor agents using National Cancer Institute (NCI) disease oriented antitumor screen protocol are investigated. Among the synthesize compounds, seventeen compounds were granted NSC code and screened at National Cancer Institute (NCI), USA for anticancer activity

  使用国家癌症研究所（NCI）疾病导向的抗肿瘤筛选方案，研究了某些2-furano-4（3 H）-喹唑啉酮，二酰胺（开环喹唑啉），喹喔啉的合成及其作为抗肿瘤剂的生物学评估。在合成的化合物中，有17种化合物被授予NSC编码，并在美国国家癌症研究所（NCI）筛选 了完整NCI 60细胞组中单一高剂量（10 -5 M）的抗癌活性。在所选化合物中，发现3-（2-氯苄亚胺）-2-（呋喃-2-基）喹唑啉-4（3h）-21是针对卵巢癌的五种剂量水平筛选中最有效的候选药物。 OVCAR-4和GI 50的非小细胞肺癌NCI-H522分别为1.82和2.14μM。合理的方法和QSAR技术使人们能够理解喹唑啉，二酰胺和喹喔啉衍生物的药效学要求。
• Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
  作者：Umesh A. Kshirsagar、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tetlet.2007.03.032

  日期：2007.4

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and anti-inflammatory activity of 2,3-diaryl-4(3H)-quinazolinones
  作者：M. R. Yadav、S. T. Shirude、A. Parmar、R. Balaraman、R. Giridhar

  DOI：10.1007/s10593-006-0201-4

  日期：2006.8
• Synthesis of 3-Substituted and 2,3-Disubstituted Quinazolinones via Cu-Catalyzed Aryl Amidation
  作者：Lanting Xu、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol300084v

  日期：2012.2.17

  Cul/4-hydroxy-L-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 degrees C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.
• Recyclable Keggin Heteropolyacids as an Environmentally Benign Catalyst for the Synthesis of New 2-Benzoylamino-N-phenyl-benzamide Derivatives under Microwave Irradiations at Solvent-Free Conditions and the Evaluation of Biological Activity
  作者：Karima Ighilahriz-Boubchir、Baya Boutemeur-Kheddis、Cherifa Rabia、Malika Makhloufi-Chebli、Maamar Hamdi、Artur Silva

  DOI：10.3390/molecules23010008

  日期：——

  a Keggin-type heteropolyacids series (H3PW12O40·13H2O; H4SiW12O40·13H2O; H4SiMo12O40·13H2O; and H3PMo12O40·13H2O) as catalysts without solvent and under microwave irradiation. We found that the use of H3PW12O40·13H2O acid coupled to microwave irradiation allowed obtaining a high-yielding reaction with a short time. The compound structures were established by 1H-NMR and 13C-NMR. The antibacterial and

  2-苯甲酰氨基-N-苯基-苯甲酰胺衍生物 (5a-h) 由 2-苯基-3,1-(4H)-苯并恶嗪-4-one 3 和取代的苯胺 4a-h 在 Keggin 型存在下制备杂多酸系列（H3PW12O40·13H2O；H4SiW12O40·13H2O；H4SiMo12O40·13H2O；和H3PMo12O40·13H2O）作为催化剂，无溶剂和微波辐射。我们发现使用H3PW12O40·13H2O酸与微波辐射耦合可以在短时间内获得高产率反应。化合物结构由1H-NMR和13C-NMR确定。合成化合物的抗菌和抗真菌活性表现出抑制细菌和真菌的生长。