2-oxo-1,2-diphenylethyl-2-chloroacetate | 51891-89-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-oxo-1,2-diphenylethyl-2-chloroacetate
• 英文别名: (2-Oxo-1,2-diphenylethyl) 2-chloroacetate
• CAS: 51891-89-5
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: RWXILKTWIZUXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-diphenylethyl-2-chloroacetate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-(chloromethyl)-4,5-diphenyloxazole
  参考文献：
  名称：

  1,2,3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation

  摘要：

  The development and use of small-molecule inhibitors of the adherence of Porphyromonas gingivalis to oral streptococci represents a potential therapy for the treatment of periodontal disease as these organisms work in tandem to colonize the oral cavity. Earlier work from these laboratories demonstrated that a small synthetic peptide was an effective inhibitor of the interaction between P. gingivalis and Streptococcus gordonii and that a small-molecule peptidomimetic would provide a more stable, less expensive and more effective inhibitor. An array of 2-(azidomethyl)- and 2-(azidophenyl)-4,5-diaryloxazoles having a full range of hydrophobic groups were prepared and reacted with substituted arylacetylenes to afford the corresponding 'click' products. The title compounds were evaluated for their ability to inhibit P. gingivalis' adherence to oral streptococci and several were found to be inhibitory in the range of (IC50) 5.3-67 mu M. (C) 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.orgilicensesiby-nc-nd/4.0/).

  DOI：

  10.1016/j.bmc.2016.08.059
• 作为产物：
  描述：

  安息香精油 、 氯乙酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2-oxo-1,2-diphenylethyl-2-chloroacetate
  参考文献：
  名称：

  [EN] ANTI-BIOFILM COMPOUNDS
  [FR] COMPOSÉS ANTI-BIOFILM

  摘要：

  本发明提供了式(I)的非肽化合物，其中：X为-(C1-C8)烷基，芳基或-芳基(C1-C8)烷基-；Y为-(C1-C8)烷基或不存在；W为杂环芳基，(C3-C7)碳环或芳基，其中W的任何杂环芳基，(C3-C7)碳环或芳基可以选择性地用一个或多个(Z1)基团取代；R1为(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可以选择性地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，-CN，NO2，卤素，-ORa，-SRa，-S(O)2NRbRc，-NRbRc，-NRaCORd，-C(O)Ra，-C(O)ORa和-C(O)NRbRc基团中的一个或多个取代；R2为(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可以选择性地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，-CN，NO2，卤素，-ORe，-SRe，-S(O)2NRfRg，-NRfRg，-NReCORh，-C(O)Re，-C(O)ORe和-C(O)NRfRg基团中的一个或多个取代；I模拟链球菌SspB粘附区（BAR）并作为P. gingivalis粘附于链球菌的抑制剂。该发明还提供了制备和使用这些抑制剂的方法。

  公开号：

  WO2013016206A1

文献信息

• Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds
  作者：Pravin C. Patil、Frederick A. Luzzio、Donald R. Demuth

  DOI：10.1016/j.tetlet.2014.11.014

  日期：2015.6

  New routes to 2, 4, 5-trisubstituted oxazoles were established whereby the substitution pattern was established by the structure of the starting nonsymmetrical acyloins. 2-Chloromethyl-4, 5-disubstituted oxazoles were prepared by refinements of an earlier described process whereby chloroacetyl esters of symmetrical and non-symmetrical acyloins were cyclized using an ammonium acetate/acetic acid protocol

  建立了形成2、4、5-三取代的恶唑的新途径，从而通过起始的不对称酰基胞苷的结构建立了取代模式。通过改进先前描述的方法制备2-氯甲基-4，5-二取代的恶唑，其中使用乙酸铵/乙酸方案将对称和不对称酰基的氯乙酰基酯环化。进行取代后，然后在温和条件下通过取代安装叠氮化物部分。尽管需要二溴化和碘化的苯基恶唑进行进一步的合成修饰，但发现环化反应对原料中卤素的相对位置非常敏感。
• ANTI-BIOFILM COMPOUNDS
  申请人：Demuth Donald R.

  公开号：US20140161845A1

  公开（公告）日：2014-06-12

  The present invention provides non-peptide compounds of formula (I) wherein: X is —(C 1 -C 8 )allcyl-, aryl or -aryl(C 1 -C 8 )alkyl-; Y is —(C 1 -C 8 )alkyl- or absent; W is heteroaryl, (C 3 -C 7 )carbocycle or aryl, wherein any heteroaryl, (C 3 -C 7 )carbocycle or, aryl of W is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z 1 groups; R 1 is (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) groups selected from (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 7 )carbocycle, halo(C 1 -C 3 )alkyl, —CN, NO 2 , halogen, —OR a , —SR a , —S(O) 2 NR b R c , —NR b R c , —NR a COR d , —C(O)R a , —C(O)OR a , and —C(O)NR b R c ; R 2 is (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )Jalkynyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) groups selected from (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 7 )carbocycle, halo(C 1 -C 3 )alkyl, —CN, NO 2 , halogen, —OR e , —SR e , —S(O) 2 NR f R g , —NR f R g —NR e COR h , —C(O)R e , —C(O)OR e and —C(O)NR f R g ; I that mimic the streptococcal; SspB Adherence Region (BAR) and function as inhibitors of P. gingivalis adherence to streptococci. The invention also provides methods of making and using the inhibitors.

  本发明提供了化合物(I)的非肽类衍生物，其中：X是—(C1-C8)烷基，芳基或-芳基(C1-C8)烷基-; Y是—(C1-C8)烷基或不存在; W是杂环芳基，(C3-C7)碳环或芳基，其中W的任何杂环芳基，(C3-C7)碳环或芳基可选择地用一个或多个(Z1)基团取代; R1是(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可选择地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，—CN，NO2，卤素，—ORa，—SRa，—S(O)2NRbRc，—NRbRc，—NRaCORd，—C(O)Ra，—C(O)ORa和—C(O)NRbRc基团中的一个或多个取代; R2是(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基或芳基，其中芳基可选择地用一个或多个(C1-C8)烷基，(C2-C8)烯基，(C2-C8)炔基，(C3-C7)碳环，卤代(C1-C3)烷基，—CN，NO2，卤素，—ORe，—SRe，—S(O)2NRfRg，—NRfRg—NReCORh，—C(O)Re，—C(O)ORe和—C(O)NRfRg基团中的一个或多个取代; I模拟链球菌SspB粘附区(BAR)，并作为P. gingivalis粘附到链球菌的抑制剂。本发明还提供制备和使用抑制剂的方法。
• Preparation of azidoaryl- and azidoalkyloxazoles for click chemistry
  作者：Catherine M. Loner、Frederick A. Luzzio、Donald R. Demuth

  DOI：10.1016/j.tetlet.2012.08.032

  日期：2012.10

  A series of azidoaryl- and azidoalkyl(diphenyl)oxazole scaffolds were warranted for biofilm inhibition studies. Cyclization of azidoaryl- or azidoalkyl esters of benzoin with ammonium acetate in acetic acid gives 2-azidoaryl- or 2-azidoalkyl-4,5-diphenyloxazoles. The azidoaryl esters are prepared from the corresponding azidocarboxylic acids/acid chlorides while the azidoalkyl esters are prepared from the corresponding haloalkyl esters. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel N-4-Piperazinyl Ciprofloxacin-Ester Hybrids: Synthesis, Biological Evaluation, and Molecular Docking Studies
  作者：A. Shahbazi、H. Mostafavi、G. Zarrini、M. Mahdavi

  DOI：10.1134/s1070363220080265

  日期：2020.8

  A series of novelN-4-piperazinyl ciprofloxacin-ester hybrids has been synthesized and the structures confirmed by(1)H and(13)C NMR, FT-IR spectral data, and elemental analysis. The products have been testedin vitrofor their antibacterial activity against six bacterial strains (MRSA,Staphylococcus epidermidis,Bacillus subtilis,Escherichia coli,Salmonella enterica, andKlebsiella pneumoniae) and have demonstrated good antibacterial activity with MIC values range 6.25-200 mu g/mL. Antifungal and cytotoxic activities of the products have been tested againstCandida kefyrand human leukemia K562 cell line, respectively. All compounds inhibit growth of K562 cells more efficiently than the parent ciprofoxacin in a dose- and duration-dependent way. Molecular docking studies performed for the compound3iindicates that similarly to ciprofloxacin it can act as an inhibitor ofS. aureusDNA gyrase.
• US9167820B2
  申请人：——

  公开号：US9167820B2

  公开（公告）日：2015-10-27