4-O-m-anisoyl-α-hydroxytetralone | 1370009-34-9

• 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: 4-O-m-anisoyl-α-hydroxytetralone
• 英文别名: 4-O-m-anisoyl-α-tetralone；[(1S)-4-oxotetralin-1-yl] 3-methoxybenzoate；[(1S)-4-oxo-2,3-dihydro-1H-naphthalen-1-yl] 3-methoxybenzoate
• CAS: 1370009-34-9
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: KRUDBHOKZNBBJK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲酰氯 、 (+)-4-hydroxy-1-tetralone 在 吡啶 、 4-二甲氨基吡啶 作用下， 以88%的产率得到4-O-m-anisoyl-α-hydroxytetralone
  参考文献：
  名称：

  Anti-tubercular agents from Ammannia baccifera (Linn.)

  摘要：

  Ammannia baccifera is an important component of various traditional Chinese herbal formulations. The samples of A. baccifera were extracted with methanol and the methanolic extract was successively fractionated with n-hexane, chloroform and n-butanol. The serial chromatographic separation of chloroform and n-butanol fractions resulted in the isolation and characterization of betulinic acid (1), 4-hydroxy-alpha-tetralone (2), tetralone-4-O-beta-D-glucopyranoside (3) and ellagic acid (4). Further, the compound 2 was chemically modified into its five semi-synthetic acyl and aryl derivatives (2A-2E) namely; 4-O-m-anisoyl-alpha-tetralone (2A), 4-O-benzoyl-alpha-tetralone (2B), 4-O-palmitoyl-alpha-tetralone (2C), 4-O-(3,4,5-trimethoxybenzoyl)-alpha-tetralone (2D) and 4-O-myricitoyl-alpha-tetralone (2E). The tetralone group compounds 2, 3 and semi-synthetic derivatives 2A-2E were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv by BACTEC-460 radiometric susceptibility assay. The compounds 2 and 2E have shown significant anti-tubercular activity (MIC 50 mu g/ml) while 2B was moderate active (MIC 100 mu g/ml) against the pathogen. The results of SAR study indicated that substitutions in alpha hydroxyl group of 4-hydroxy-alpha-tetralone either retards or have no increasement in in vitro anti-tubercular potential.

  DOI：

  10.1007/s00044-012-9998-9

文献信息

• Anti-tubercular agents from Ammannia baccifera (Linn.)
  作者：Harish C. Upadhyay、Jay Prakash Thakur、Dharmendra Saikia、Santosh K. Srivastava

  DOI：10.1007/s00044-012-9998-9

  日期：2013.1

  Ammannia baccifera is an important component of various traditional Chinese herbal formulations. The samples of A. baccifera were extracted with methanol and the methanolic extract was successively fractionated with n-hexane, chloroform and n-butanol. The serial chromatographic separation of chloroform and n-butanol fractions resulted in the isolation and characterization of betulinic acid (1), 4-hydroxy-alpha-tetralone (2), tetralone-4-O-beta-D-glucopyranoside (3) and ellagic acid (4). Further, the compound 2 was chemically modified into its five semi-synthetic acyl and aryl derivatives (2A-2E) namely; 4-O-m-anisoyl-alpha-tetralone (2A), 4-O-benzoyl-alpha-tetralone (2B), 4-O-palmitoyl-alpha-tetralone (2C), 4-O-(3,4,5-trimethoxybenzoyl)-alpha-tetralone (2D) and 4-O-myricitoyl-alpha-tetralone (2E). The tetralone group compounds 2, 3 and semi-synthetic derivatives 2A-2E were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv by BACTEC-460 radiometric susceptibility assay. The compounds 2 and 2E have shown significant anti-tubercular activity (MIC 50 mu g/ml) while 2B was moderate active (MIC 100 mu g/ml) against the pathogen. The results of SAR study indicated that substitutions in alpha hydroxyl group of 4-hydroxy-alpha-tetralone either retards or have no increasement in in vitro anti-tubercular potential.
• 4-Hydroxy-<i>α</i>-Tetralone and its Derivative as Drug Resistance Reversal Agents in Multi Drug Resistant<i>E</i><i>scherichia coli</i>
  作者：Gaurav R. Dwivedi、Harish C. Upadhyay、Dharmendra K. Yadav、Vigyasa Singh、Santosh K. Srivastava、Feroz Khan、Nandan S. Darmwal、Mahendra P. Darokar

  DOI：10.1111/cbdd.12263

  日期：2014.4

  The purpose of present investigation was to understand the drug resistance reversal mechanism of 4‐hydroxy‐α‐tetralone (1) isolated from Ammannia spp. along with its semi‐synthetic derivatives (1a–1e) using multidrug resistant Escherichia coli (MDREC). The test compounds did not show significant antibacterial activity of their own, but in combination, they reduced the minimum inhibitory concentration (MIC) of tetracycline (TET). In time kill assay, compound 1 and its derivative 1e in combination with TET reduced the cell viability in concentration dependent manner. Compounds 1 and 1e were also able to reduce the mutation prevention concentration of TET. Both compounds showed inhibition of ATP dependent efflux pumps. In real time polymerase chain reaction (RT‐PCR) study, compounds 1 and 1e alone and in combination with TET showed significant down expression of efflux pump gene (yojI) encoding multidrug ATP binding cassettes (ABC) transporter protein. Molecular mechanism was also supported by the in silico docking studies, which revealed significant binding affinity of compounds 1 and 1e with YojI. This study confirms that compound 1 and its derivative 1e are ABC efflux pump inhibitors which may be the basis for development of antibacterial combinations for the management of MDR infections from inexpensive natural product.