ethyl [2-(3-chlorobenzoyl)-4-methylphenoxy]acetate | 677707-45-8

• 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: ethyl [2-(3-chlorobenzoyl)-4-methylphenoxy]acetate
• 英文别名: Acetic acid, [2-(3-chlorobenzoyl)-4-methylphenoxy]-, ethyl ester；ethyl 2-[2-(3-chlorobenzoyl)-4-methylphenoxy]acetate
• CAS: 677707-45-8
• 化学式: C₁₈H₁₇ClO₄
• 分子量: 332.784
• InChiKey: XKEPGNNQYWZMMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  ethyl [2-(3-chlorobenzoyl)-4-methylphenoxy]acetate 在 氢氧化钾 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 (3-chlorophenyl)-[5-methyl-2-[(2-thioxo-3H-1,3,4-oxadiazol-5-yl)methoxy]phenyl]methanone
  参考文献：
  名称：

  Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones

  摘要：

  The triazolothiadiazine analogues 6a-e were obtained via a multistep synthesis sequences beginning with the hydroxybenzophenones la-e. Hydroxybenzophenones on reaction with ethyl chloroacetate affords ethyl (2-aroylarytoxy)acetates 2a-e which on treatment with hydrazine hydrate yields 2-(2-aroylaryloxy)acetohydrazides 3a-e. Intramolecular cyclization of 3a-e with carbon disulfide affords 5-(2-aroylaryloxy)methyl-1,3,4-oxadiazole-2-(3H)thiones 4a-e, which on treatment with hydrazine hydrate yields 4-amino-5-(2-aroyl aryloxy)methyl-1,2,4-triazole-3-(2H)thiones 5a-e. Condensation of 5a-e with alpha-halocarbonyl compound results in 3-(2-aroylaryloxy)methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine 6a-e analogues. The compounds 4a-e, 5a-e and 6a-e were tested against variety of fungal and bacterial strains in comparison to fluconazole and chloramphenicol, respectively. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.005
• 作为产物：
  描述：

  4-methylphenyl 3-chlorobenzoate 在 三氯化铝 、 potassium carbonate 作用下， 以 硝基苯 、 丙酮 为溶剂， 反应 8.5h， 生成 ethyl [2-(3-chlorobenzoyl)-4-methylphenoxy]acetate
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of benzophenone analogues

  摘要：

  A series of substituted benzophenone analogues has been synthesized and evaluated as orally active anti-inflammatory agents with reduced side effects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin, and phenylbutazone. In carrageenan-induced foot pad edema assay, benzophenone analogues showed an interesting anti-inflammatory activity. In the air-pouch test, some of the analogues reduced the total number of leukocytes of the exudate, which indicates inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, in the liver and stomach. None of the compounds showed significant side effects compared with nonsteroidal anti-inflammatory drugs such as indomethacin and naproxen. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.04.003

文献信息

• Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis
  作者：B.R. Vijay Avin、Prabhu Thirusangu、V. Lakshmi Ranganatha、Aiyesha Firdouse、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2014.01.050

  日期：2014.3

  A sequence of coumarin analogs 5a–j was obtained by multi step synthesis from hydroxy benzophenones (1a–j). The in vitro antiproliferative effect of the title compounds was tested against Ehrlich ascites carcinoma (EAC) and Daltons lymphoma ascites (DLA) cell lines. Among the series, compound 5c with bromo group in the benzophenone moiety was endowed with excellent antiproliferative potency with significant

  通过多步合成从羟基二苯甲酮（1a – j）获得了香豆素类似物5a – j的序列。在体外的标题化合物的抗增殖作用是对艾氏腹水癌（EAC）和道尔顿淋巴瘤腹水（DLA）细胞系进行测试。在该系列中，在二苯甲酮部分中具有溴基的化合物5c具有出色的抗增殖潜能，IC 50值很高。此外，化合物5c对鼠EAC和实体DL肿瘤模型系统的体内抗肿瘤作用通过延长的存活期得到证实。复方的抑瘤机制5c是由于抗血管生成和促进细胞凋亡。这些结果表明化合物5c的可能应用，其可以在不久的将来被开发为有效的抗癌药。
• Microwave-assisted synthesis of 2-amino and 2-azetidinonyl 5-(2-benzoyl-phenoxymethyl) 1,3,4-oxadiazoles
  作者：Shaukath Ara Khanum、S. Shashikanth、B. S. Sudha

  DOI：10.1002/hc.10210

  日期：——

  A simple high yielding method for the integration of heterocyclic rings viz. 1,3,4-oxadiazole and azetidin-2-one at the benzophenone nucleus has been developed starting from substituted 2-hydroxybenzophenones, and by using mild conditions, wet solid surface, and microwave irradiation. A comparison of this microwave-accelerated reaction with conventional heating condition is also illustrated. © 2003

  一种简单的高产杂环整合方法，即。二苯甲酮核上的 1,3,4-恶二唑和氮杂环丁烷-2-one 已从取代的 2-羟基二苯甲酮开始，并通过使用温和的条件、湿固体表面和微波辐射开发出来。还说明了这种微波加速反应与常规加热条件的比较。© 2003 Wiley Periodicals, Inc. 杂原子化学 15:37–42, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10210
• Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles
  作者：V. Girish、Noor Fatima Khanum、H. D. Gurupadaswamy、Shaukath Ara Khanum

  DOI：10.1134/s1068162014030066

  日期：2014.5

  Synthetic pathway of the ten novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles as new potential antimicrobial agents is illustrated. Intramolecular cyclization of 2-(2-aroylaryloxy) aceto hydrazides to 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles was achieved with triethyl orthoformate in good yields. The compounds were characterized by IR, H-1 NMR, mass spectra and by means of CHN analysis. The target compounds were tested for their in vitro antimicrobial activity against representative strains by disc diffusion method and micro dilution methods. Several compounds showed antimicrobial activity comparable with or higher than the standard drugs.
• Anti-tumor and proapoptotic effect of novel synthetic benzophenone analogues in Ehrlich ascites tumor cells
  作者：B.T. Prabhakar、Shaukath Ara Khanum、K. Jayashree、Bharathi P. Salimath、S. Shashikanth

  DOI：10.1016/j.bmc.2005.08.039

  日期：2006.1

  A series of substituted benzophenone analogues, (2-aroyl-4-methylphenoxy)acetamides 4a-e, have been synthesized via three-step synthesis sequence beginning with the 2-hydroxybenzophenones la-a in excellent yield. la-a on reaction with ethyl chloroacetate afford ethyl (2-aroyl-4-methylphenoxy)acetates 2a-e which on alkaline hydrolysis afforded (2-aroyl-4-methylphenoxy)ethanoic acid 3a-e. Compounds 3a-e on condensation with p-chloroaniline furnished benzophenone analogues 4a-e. In the present report, we investigated the anti-tumor and proapoptotic effect of benzophenones in Ehrlich ascites tumor (EAT) cells. Treatment of benzophenones in vivo resulted in inhibition of proliferation of EAT cells and ascites formation. Further, we demonstrate that the induction of apoptosis in EAT cells is mediated through activation of caspase-3. These results suggest a further possible clinical application of these synthetic compounds as potent anti-tumor and proapoptotic compounds. (c) 2005 Elsevier Ltd. All rights reserved.