3-(4'-methylbenzoyl)benzoic acid | 65414-18-8

• 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: 3-(4'-methylbenzoyl)benzoic acid
• 英文别名: 3-(4-methylbenzoyl)benzoic acid；3-p-toluoyl-benzoic acid；4'-Methyl-benzophenon-carbonsaeure-(3)；3-p-Toluoyl-benzoesaeure；3-p-Toluyl-benzoesaeure；3-(4-Methylbenzoyl)benzoesaeure；3-(4-Methylbenzoyl)benzoic acid
• CAS: 65414-18-8
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: IIOKLIRIXVUUSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4'-methylbenzoyl)benzoic acid 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-(3-(4-methylbenzoyl)benzoyl)-3-thiosemicarbazide
  参考文献：
  名称：

  3-Mercapto-1,2,4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors

  摘要：

  The production of beta-lactamases is an effective strategy by which pathogenic bacteria can develop resistance against beta-lactam antibiotics. While inhibitors of serine-beta-lactamases are widely used in combination therapy with b-lactam antibiotics, there are no clinically available inhibitors of metallo-beta-lactamases (MBLs), and so there is a need for the development of such inhibitors. This work describes the optimisation of a lead inhibitor previously identified by fragment screening of a compound library. We also report that thiosemicarbazide intermediates in the syntheses of these compounds are also moderately potent inhibitors of the IMP-1 MBL from Pseudomonas aeruginosa. The interactions of these inhibitors with the active site of IMP-1 were examined using in silico methods. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.116
• 作为产物：
  描述：

  3-(氯羰基)苯甲酸甲酯 在 sodium hydroxide 、 三氯化铝 作用下， 以 水 为溶剂， 反应 12.0h， 生成 3-(4'-methylbenzoyl)benzoic acid
  参考文献：
  名称：

  芳基过苯甲酸叔丁酯的合成，晶体结构和激光闪光光解。

  摘要：

  合成了芳基过苯甲酸叔丁酯（1-7）。2和5的单晶结构表明，过酸酯和二苯甲酮的羰基几乎彼此共面。CCl4中1-5的激光闪光光解（LFP，lambdaex = 355 nm）产生相应的芳酰基苯基自由基（9-13）。对芳酰基取代的苯基（9-12）的寿命是相似的（约0.4微米），但每个寿命都比间芳酰基取代的苯基（13）短。2、6和7的LFP还会产生不同的（叔丁基二氧羰基苯甲酰基）苄基（8、14和15，λ最大约为320 nm）。已发现每种CCl4的寿命约为17-18微米。讨论了取代基对1-7分解的量子产率和9-13的寿命的影响。

  DOI：

  10.1021/jo030168d

文献信息

• Laser Flash Photolysis of <i>tert</i>-Butyl Aroylperbenzoates:  Kinetics of the Singlet and Triplet States and the Aroylphenyl Radicals¹
  作者：Bipin K. Shah、Douglas C. Neckers

  DOI：10.1021/ja030231g

  日期：2004.2.1

  aroylperbenzoates (1−4) were studied by laser flash photolysis (LFP). LFP (380 nm, pulse width ∼350 fs) of 2 and 3 allowed direct observation of their singlet states, which showed broad absorption (λmax ∼ 625 nm; τ ∼ 20 and ∼7.9 ps, respectively). The triplet state of each (λmax ∼ 530−560 nm) rapidly dissociates by O−O cleavage as indicated by the short triplet lifetimes (e.g., triplet lifetime of 3 ∼0.74 ns). The

  通过激光闪光光解 (LFP) 研究了叔丁基芳酰基过苯甲酸酯 (1-4)。2 和 3 的 LFP（380 nm，脉冲宽度 ∼350 fs）允许直接观察它们的单线态，显示出广泛的吸收（λmax ∼ 625 nm；τ ∼ 20 和 ∼7.9 ps，分别）。每个（λmax ∼ 530-560 nm）的三重态通过 O-O 裂解迅速解离，如三重态寿命短（例如，三重态寿命为 3 ∼0.74 ns）所示。从 1、2 和 4 的 355 nm LFP（脉冲宽度~7 ns）获得的~550 nm 吸收已分配给相应的芳酰基苯基。详细研究的两个代表性基团（4-苯甲酰基苯基 5 和 3-（4'-甲基苯甲酰基）苯基 6）显示出依赖于溶剂的寿命。已观察到这些自由基与各​​种猝灭剂（包括含双键单体）反应的绝对双分子速率常数在室温下在 CCl4 中为 7.56 × 107 至 1.68 × 109 M-1 s-1。芳酰基苯基自由基的可能结构和负责的转变
• Penicillin inhibitors of purple acid phosphatase
  作者：Faridoon、Waleed M. Hussein、Nazar Ul Islam、Luke W. Guddat、Gerhard Schenk、Ross P. McGeary

  DOI：10.1016/j.bmcl.2012.01.123

  日期：2012.4

  Purple acid phosphatases (PAPs) are binuclear metallohydrolases that have a multitude of biological functions and are found in fungi, bacteria, plants and animals. In mammals, PAP activity is linked with bone resorption and over-expression can lead to bone disorders such as osteoporosis. PAP is therefore an attractive target for the development of drugs to treat this disease. A series of penicillin conjugates, in which 6-aminopenicillanic acid was acylated with aromatic acid chlorides, has been prepared and assayed against pig PAP. The binding mode of most of these conjugates is purely competitive, and some members of this class have potencies comparable to the best PAP inhibitors yet reported. The structurally related penicillin G was shown to be neither an inhibitor nor a substrate for pig PAP. Molecular modelling has been used to examine the binding modes of these compounds in the active site of the enzyme and to rationalise their activities. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• FRIEDEL AND CRAFTS' REACTION. THE CARBOMETHOXY-BENZOYL CHLORIDES WITH AROMATIC HYDROCARBONS AND ALUMINUM CHLORIDE.
  作者：Maurice E. Smith

  DOI：10.1021/ja01441a020

  日期：1921.8
• Hoornaert,G.; Slootmaekers,P.J., Bulletin des Societes Chimiques Belges, 1968, vol. 77, p. 295 - 313
  作者：Hoornaert,G.、Slootmaekers,P.J.

  DOI：——

  日期：——
• 3-Mercapto-1,2,4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors
  作者：Faridoon、Waleed M. Hussein、Peter Vella、Nazar Ul Islam、David L. Ollis、Gerhard Schenk、Ross P. McGeary

  DOI：10.1016/j.bmcl.2011.10.116

  日期：2012.1

  The production of beta-lactamases is an effective strategy by which pathogenic bacteria can develop resistance against beta-lactam antibiotics. While inhibitors of serine-beta-lactamases are widely used in combination therapy with b-lactam antibiotics, there are no clinically available inhibitors of metallo-beta-lactamases (MBLs), and so there is a need for the development of such inhibitors. This work describes the optimisation of a lead inhibitor previously identified by fragment screening of a compound library. We also report that thiosemicarbazide intermediates in the syntheses of these compounds are also moderately potent inhibitors of the IMP-1 MBL from Pseudomonas aeruginosa. The interactions of these inhibitors with the active site of IMP-1 were examined using in silico methods. (C) 2011 Elsevier Ltd. All rights reserved.