2-hydroxy-N-(4-methylbenzoyl)benzamide | 57135-18-9

• 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: 2-hydroxy-N-(4-methylbenzoyl)benzamide
• 英文别名: N-(4-methylbenzoyl)salicylamide；MP-IV-29；2-hydroxy-4'-methyl-dibenzamide；2-hydroxy-N-(4-methyl-benzoyl)-benzamide；N-p-Toluoylsalicylamid
• CAS: 57135-18-9
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: SKGOHGZRLCHLAD-UHFFFAOYSA-N

物化性质

• 熔点：
  196-196.5 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  472.9±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-(4-methylbenzoyl)benzamide 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 盐酸羟胺 、 sodium acetate 、 sodium hydride 、 苯甲醚 、 三氟乙酸 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-3-[[[1-[[4-[5-(2-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyridinium-4-yl]thio]methyl]-8-oxo-1-aza-5-thiabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

  摘要：

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00261-8
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 水杨酰胺 在 吡啶 作用下， 反应 4.0h， 以85%的产率得到2-hydroxy-N-(4-methylbenzoyl)benzamide
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure–Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania

  摘要：

  In our efforts to identify novel chemical scaffolds for the development of new antiprotozoal drugs, a compound library was screened against Toxoplasma gondii tachyzoites with activity discovered for N-(4-ethylbenzoyl)-2-hydroxybenzamide la against T. gondii as described elsewhere. Synthesis of a compound set was guided by T. gondii SAR with 1r found to be superior for T. gondii, also active against Thai and Sierra Leone strains of Plasmodium falciparum, and with superior ADMET properties as described elsewhere. Herein, synthesis methods and details of the chemical analysis of the compounds in this series are described. Further, this series of N-benzoyl-2-hydroxybenzamides was repurposed for testing against four other protozoan parasites: Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, and P. falciparum (K1 isolate). Structure-activity analyses led to the identification of compounds in this set with excellent antileishmanial activity (compound 1d). Overall, compound 1r was the best and had activity 21-fold superior to that of the standard antimalarial drug chloroquine against the K1 P. falciparum isolate.

  DOI：

  10.1021/jm2015183

文献信息

• Ryabukhin, Yu. I.; Faleeva, L. N.; Gorbunova, M. O., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 9, p. 1794 - 1800
  作者：Ryabukhin, Yu. I.、Faleeva, L. N.、Gorbunova, M. O.、Kovaleva, T. V.、Uflyand, I. E.、Sheinker, V. N.

  DOI：——

  日期：——
• Uflyand, I. E.; Ryabukhin, Yu. I.; Vysotskii, B. D., Koordinatsionnaya Khimiya, 1982, vol. 8, p. 501 - 506
  作者：Uflyand, I. E.、Ryabukhin, Yu. I.、Vysotskii, B. D.、Askalepov, V. N.、Kurbatov, V. P.

  DOI：——

  日期：——
• Dorofeenko,G.N. et al., Journal of general chemistry of the USSR, 1975, vol. 45, p. 1823 - 1825
  作者：Dorofeenko,G.N. et al.

  DOI：——

  日期：——
• DOROFEENKO G. N.; RYABUXIN YU. I.; MEZHERITSKIJ V. V., ZH. OBSHCH. XIMII <ZOKN-A4>, 1975, 45, HO 8, 1860-1862
  作者：DOROFEENKO G. N.、 RYABUXIN YU. I.、 MEZHERITSKIJ V. V.

  DOI：——

  日期：——
• RYABUXIN, YU. I.;FALEEVA, L. N.;GORBUNOVA, M. O.;KOVALEVA, T. V.;UFLYAND,+, ZH. ORGAN. XIMII, 24,(1988) N 9, S. 1990-1997
  作者：RYABUXIN, YU. I.、FALEEVA, L. N.、GORBUNOVA, M. O.、KOVALEVA, T. V.、UFLYAND,+

  DOI：——

  日期：——