1,3-dipropanoylchloramphenicol | 1304534-01-7

• 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: 1,3-dipropanoylchloramphenicol
• 英文别名: (1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(propanoyloxy)propyl propanoate；(2'R,3'R)-chloramphenicol 1',3'-dipropanoate；Acetamide, 2,2-dichloro-N-[(1R,2R)-2-(4-nitrophenyl)-2-(1-oxopropoxy)-1-[(1-oxopropoxy)methyl]ethyl]-；[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-(4-nitrophenyl)-3-propanoyloxypropyl] propanoate
• CAS: 1304534-01-7
• 化学式: C₁₇H₂₀Cl₂N₂O₇
• 分子量: 435.261
• InChiKey: MKEIIBSGKANDBN-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-dipropanoylchloramphenicol 在 Novozym 435 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到1-propanoylchloramphenicol
  参考文献：
  名称：

  Enzymatic regioselective production of chloramphenicol esters

  摘要：

  An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.070
• 作为产物：
  描述：

  [(2R,3R)-3-乙酰氧基-2-[(2,2-二氯乙酰基)氨基]-3-(4-硝基苯基)丙基]乙酸酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 1,3-dipropanoylchloramphenicol
  参考文献：
  名称：

  Enzymatic regioselective production of chloramphenicol esters

  摘要：

  An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.070

文献信息

• Chloramphenicol Derivatives with Antibacterial Activity Identified by Functional Metagenomics
  作者：Shamima Nasrin、Suresh Ganji、Kavita S. Kakirde、Melissa R. Jacob、Mei Wang、Ranga Rao Ravu、Paul A. Cobine、Ikhlas A. Khan、Cheng-Cang Wu、David A. Mead、Xing-Cong Li、Mark R. Liles

  DOI：10.1021/acs.jnatprod.7b00903

  日期：2018.6.22

  A functional metagenomic approach identified novel and diverse soil-derived DNAs encoding inhibitors to methicillin-resistant Staphylococcus aureus (MRSA). A metagenomic DNA soil library containing 19 200 recombinant Escherichia coli BAC clones with 100 Kb average insert size was screened for antibiotic activity. Twenty-seven clones inhibited MRSA, seven of which were found by LC-MS to possess modified chloramphenicol (Cm) derivatives, including three new compounds whose structures were established as 1-acetyl-3-propanoylchloramphenicol, 1-acety1-3-butanoyl-chloramphenicol, and 3-butanoyl-1-propanoylchloramphenicol. Cm was used as the selectable antibiotic for cloning, suggesting that heterologously expressed enzymes resulted in derivatization of Cm into new chemical entities with biological activity. An esterase was found to be responsible for the enzymatic regeneration of Cm, and the gene trfA responsible for plasmid copy induction was found to be responsible for inducing antibacterial activity in some clones. Six additional acylchloramphenicols were synthesized for structure and antibacterial activity relationship studies, with 1-p-nitrobenzoylchloramphenicol the most active against Mycobacterium intracellulare and Mycobacterium tuberculosis, with MICs of 12.5 and 50.0 mu g/mL, respectively.
• Enzymatic regioselective production of chloramphenicol esters
  作者：Ayla M.C. Bizerra、Tasso G.C. Montenegro、Telma L.G. Lemos、Maria C.F. de Oliveira、Marcos C. de Mattos、Iván Lavandera、Vicente Gotor-Fernández、Gonzalo de Gonzalo、Vicente Gotor

  DOI：10.1016/j.tet.2011.02.070

  日期：2011.4

  An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes. (C) 2011 Elsevier Ltd. All rights reserved.