(3-氯苯基)-(2-羟基-5-甲基苯基)甲酮 | 6280-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3-氯苯基)-(2-羟基-5-甲基苯基)甲酮
• 英文名称: 3'-Chlor-2-hydroxy-5-methyl-benzophenon
• 英文别名: 2-Hydroxy-5-methyl-3'-chlorbenzophenon；3'-chloro-2-hydroxy-5-methyl-benzophenone；(3-Chlorophenyl)(2-hydroxy-5-methylphenyl)methanone；(3-chlorophenyl)-(2-hydroxy-5-methylphenyl)methanone
• CAS: 6280-54-2
• 化学式: C₁₄H₁₁ClO₂
• 分子量: 246.693
• InChiKey: LGAUSQYBRVKFEO-UHFFFAOYSA-N

物化性质

• 熔点：
  72°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-氯苯基)-(2-羟基-5-甲基苯基)甲酮 在 氢氧化钾 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 17.0h， 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 作用下， 以 硝基苯 为溶剂， 反应 0.75h， 以90%的产率得到(3-氯苯基)-(2-羟基-5-甲基苯基)甲酮
  参考文献：
  名称：

  二苯甲酮衍生物的合成和晶体学分析-潜在的抗炎药。

  摘要：

  以优异的产率实现了取代苯甲酸苯酯1a-j到取代羟基二苯甲酮2a-j的弗里斯重排。2a-j进一步苯甲酰化为苯甲酰氧基二苯甲酮4a-n，二苯甲酮类似物，收率良好。评价所有新合成的化合物的抗炎活性，并与标准药物进行比较。在所研究的化合物中，对位带有氯和甲基取代基的化合物4c，4e，4g，4h和4k在所有测试剂量下均比标准药物具有更强的活性。

  DOI：

  10.1016/j.bmc.2007.02.051

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。
• Design, synthesis and molecular docking of benzophenone conjugated with oxadiazole sulphur bridge pyrazole pharmacophores as anti inflammatory and analgesic agents
  作者：Zabiulla、A.R. Gulnaz、Yasser Hussein Eissa Mohammed、Shaukath Ara Khanum

  DOI：10.1016/j.bioorg.2019.103220

  日期：2019.11

  active lipid compounds having diverse hormone like effects are important mediators of the body’s response to pain and inflammation, and are formed from essential fatty acids found in cell membranes. This reaction is catalyzed by cyclooxygenase, a membrane associated enzyme occurring in two isoforms, COX-1 and COX-2. Nonsteroidal anti-inflammatory drugs (NSAIDs) act by inhibiting the activity of COX.

  前列腺素（PG）是一组具有多种激素样作用的生理活性脂质化合物，是人体对疼痛和炎症反应的重要介体，由细胞膜中的必需脂肪酸形成。该反应由环氧合酶催化，环氧合酶是一种与膜相关的酶，以两种同工型COX-1和COX-2发生。非甾体类抗炎药（NSAIDs）通过抑制COX的活性发挥作用。鉴于此，设计，合成，表征并随后评价了与恶二唑硫桥吡唑部分8a-1缀合的一系列新型二苯甲酮的抗炎和镇痛特性。新型类似物8a-1的研究对潜在的抗炎活性显示出高水平的COX-1和COX-2抑制活性。在该系列中，化合物8i在二苯甲酮的苯甲酰基环的对位具有吸电子氟基团，其特征在于对COX-1和COX-2的抑制均具有最高的IC 50值，这与标准药物相当。此外，已经对有效化合物进行了分子对接研究。
• 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 of some newer analogues of substituted dibenzoyl phenol as potent anti-inflammatory agents
  作者：Shaukath Ara. Khanum、Venu T. D、Sheena Shashikanth、Aiysha Firdouse

  DOI：10.1016/j.bmcl.2004.08.014

  日期：2004.11

  3a-f, which on Fries rearrangement using microwave irradiation led to a facile synthesis of solely dibenzoyl phenols 4a-f in excellent yield. The newly synthesized compounds were screened for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied, the compound 4e showed more potent activity than the standard drugs at all doses tested.

  羟基二苯甲酮1a-f的苯甲酰化作用提供了取代的苯甲酰基苯基苯甲酸酯3a-f，使用微波辐射进行弗里斯重排后，可以轻松地以优异的产率轻松合成仅二苯甲酰基苯酚4a-f。筛选新合成的化合物的抗炎活性，并与标准药物进行比较。在所研究的化合物中，化合物4e在所有测试剂量下均显示出比标准药物更强的活性。
• 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.