de-6-MSA-pactamycin | 1073233-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: de-6-MSA-pactamycin
• 英文别名: De-6-methylsalicylyl pactamycin；3-[(1R,2R,3S,4S,5S)-4-(3-acetylanilino)-5-amino-2,3-dihydroxy-1-[(1S)-1-hydroxyethyl]-3-(hydroxymethyl)-2-methylcyclopentyl]-1,1-dimethylurea
• CAS: 1073233-89-2
• 化学式: C₂₀H₃₂N₄O₆
• 分子量: 424.497
• InChiKey: ZBMYQXMIVFKMOG-QRIIJPHXSA-N

物化性质

• 沸点：
  708.8±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  168
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1'S,2'R,4R,4'R,5S,5'S)-4'-azido-1'-(hydroxymethyl)-2-(4-methoxyphenyl)-2',5-dimethylspiro[5H-1,3-oxazole-4,3'-6-oxabicyclo[3.1.0]hexane]-2'-ol 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 三氟甲磺酸酐 、 camphor-10-sulfonic acid 、 三(二甲氨基)锍二氟三甲基硅酸 、 zinc trifluoromethanesulfonate 、 二异丁基氢化铝 、 potassium carbonate 、 甲烷 、 氯化铵 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 、 三氟乙酸 、 ytterbium(III) triflate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 de-6-MSA-pactamycin
  参考文献：
  名称：

  泛霉素和乙酰氨基甲酸酯的全合成：详细说明

  摘要：

  本文介绍了合成研究，该研究最终完成了第一个完全合成的pactamycin和pactamycate，以及平行的两个已知的同类物，即de-6-MSA-pactamycin和de-6-MSA-pactamycate，它们缺少6-甲基水杨基部分。与起升苏氨酸作为凯龙，一系列导致关键环戊窝藏螺恶唑啉立体控制缩合的。一系列系统的功能化作用最初导致不正确的环戊酮环氧化物，该环戊酮在溶剂分解条件下被“转化”。其余基团的安装和恶唑啉的处理最终导致了pactamycin，pactamycate及其去水杨基类似物。

  DOI：

  10.1021/jo301638z

文献信息

• PACTAMYCIN BIOSYNTHETIC GENE CLUSTER
  申请人：Mahmud Taifo

  公开号：US20100210837A1

  公开（公告）日：2010-08-19

  This disclosure describes the molecular cloning of a pactamycin biosynthetic gene cluster from Streptomyces pactum ATCC 27456, characterization of individual genes in the gene cluster and the proteins encoded thereby as well as uses thereof. The pactamycin gene cluster is located within an 86.35 kilobases genetic locus and includes 53 open reading frames, 26 of which are considered to be the core cluster directly involved in the biosynthesis of pactamycin.
• PACTAMYCIN ANALOGS AND METHODS OF USE
  申请人：State of Oregon acting by and through the state Board of Higher Education on behalf of

  公开号：US20130231377A1

  公开（公告）日：2013-09-05

  Disclosed are pactamycin analogs, pharmaceutical compositions including the analogs, and methods of using the analogs, such as to inhibit tumor growth or a pathogenic infection such as a bacterial or parasitic infection. The pactamycin analogs have a general formula where R 1 is H, lower aliphatic, amide, acyl, or aminoacyl; R 2 is —C(O)NR 8 R 9 where R 8 and R 9 independently are hydrogen or lower aliphatic, or R 1 and R 2 together form a cyclic structure; R 3 and R 4 independently are hydrogen, hydroxyl, or lower aliphatic, or R 2 and R 3 together form a cyclic structure; R 5 is hydrogen or acyl; R 6 and R 7 independently are hydrogen, hydroxyl, halogen, lower aliphatic, or amino.
• PACTAMYCIN ANALOGS AND METHODS OF MAKING THEREOF
  申请人：Oregon State University

  公开号：US20150183730A1

  公开（公告）日：2015-07-02

  This disclosure describes the molecular cloning of a pactamycin biosynthetic gene cluster from Streptomyces pactum ATCC 27456, characterization of individual genes in the gene cluster and the proteins encoded thereby as well as uses thereof. The pactamycin gene cluster is located within an 86.35 kilobases genetic locus and includes 53 open reading frames, 26 of which are considered to be the core cluster directly involved in the biosynthesis of pactamycin. The present disclosure also relates to the use of the pactamycin biosynthetic genes located within the identified gene cluster for drug design and development purposes, including the development of pactamycin analogs that are more efficacious and less toxic. Also provided are drugs and antibiotics so produced, as well as methods of their use.
• US8957251B2
  申请人：——

  公开号：US8957251B2

  公开（公告）日：2015-02-17
• US9452976B2
  申请人：——

  公开号：US9452976B2

  公开（公告）日：2016-09-27