2-chloro-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide | 17278-57-8

• 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: 2-chloro-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide
• 英文别名: 2(R)-[N-(chloroacetyl)amino]-1(R)-p-nitrophenyl-1,3-propanediol；(1R,2R)-2-(2-chloro-acetylamino)-1-(4-nitro-phenyl)-propane-1,3-diol；(1R,2R)-2-(2-Chlor-acetylamino)-1-(4-nitro-phenyl)-propan-1,3-diol；Monochloroamphenicol；2-chloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• CAS: 17278-57-8
• 化学式: C₁₁H₁₃ClN₂O₅
• 分子量: 288.688
• InChiKey: HMZILUGWVSCMJF-MWLCHTKSSA-N

物化性质

• 沸点：
  623.3±55.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide 在 palladium on activated charcoal 吡啶 、 氢气 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 4.0h， 生成 N-[4-[(1R,2R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-1-hydroxy-2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]propyl]phenyl]benzamide
  参考文献：
  名称：

  Oligonucleotides with ( N -thymin-1-ylacetyl)-1-arylserinol backbone: chiral acyclic analogs with restricted conformational flexibility

  摘要：

  All four threo/erythro stereoisomers of 2(R/S)-(N-thymin-1-ylacetyl)-amino-1(R/S)-aryl-1,3-propanediol were synthesized from 2(R/S)-amino-1(R/S)-aryl-1,3-propanediol in 45-50% overall yield. The inversion of the C1 hydroxyl group in (1S, 2S), 4a, and (1R, 2R), 4d, was accomplished under Mitsunobu conditions to get (IR, 2S), 4c, and (1S, 2R), 4e isomers, respectively Compounds 4a-f were individually converted into their respective amidite synthons 5a-f. All these stereoisomers were individually incorporated into oligonucleotides (ODNs) at pre-determined positions and various biophysical studies of their hybrids with complementary DNA were carried out. All the four stereoisomers when present at 3'/5' terminal positions in the ODNs were almost equally efficient in their binding capacity as the natural oligomers, with (1S, 2S) being marginally favored over other stereoisomers. The incorporation of these chiral acyclic nucleosides also protected the ODN against enzymatic degradation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01099-1
• 作为产物：
  描述：

  氯霉素 在 氢气 作用下， 以 水 为溶剂， 反应 10.0h， 生成 棒状杆菌素I 、 2-chloro-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide
  参考文献：
  名称：

  Fabrication of resin supported Au–Pd bimetallic nanoparticle composite to efficiently remove chloramphenicol from water

  摘要：

  Au-Pd双金属纳米颗粒负载在amberlite 717上形成催化体系（717@Au-Pd），该体系在去除含碳-卤素键的环境污染物如氯霉素方面表现出卓越的活性。

  DOI：

  10.1039/c4ra17309k

文献信息

• Synthesis and Evaluation of Hetero- and Homodimers of Ribosome-Targeting Antibiotics: Antimicrobial Activity, in Vitro Inhibition of Translation, and Drug Resistance
  作者：Yifat Berkov-Zrihen、Keith D. Green、Kristin J. Labby、Mark Feldman、Sylvie Garneau-Tsodikova、Micha Fridman

  DOI：10.1021/jm400707f

  日期：2013.7.11

  the action of several bacterial resistance mechanisms that deactivate tobramycin and chloramphenicol. This study demonstrates that covalently linking two identical or different ribosome-targeting antibiotics may lead to (i) a broader spectrum of antimicrobial activity, (ii) improved inhibition of bacterial translation properties compared to that of the parent antibiotics, and (iii) reduction in the

  在这项研究中，我们描述了不同核糖体靶向抗生素的三种完整结构的全套同二聚体和异二聚体的合成：妥布霉素、克林霉素和氯霉素。评估了二聚体结构生物活性的几个方面，包括抗微生物活性、体外细菌蛋白质翻译的抑制，以及二聚体化对使妥布霉素和氯霉素失活的几种细菌耐药机制的作用的影响。这项研究表明，共价连接两种相同或不同的靶向核糖体的抗生素可能会导致 (i) 更广泛的抗菌活性，(ii) 与母体抗生素相比，改善对细菌翻译特性的抑制，
• Method for making nitrophenyl acylamido alkane diols
  申请人：PARKE DAVIS & CO

  公开号：US02483884A1

  公开（公告）日：1949-10-04