H-Ser(1)-D-Dab(Cbz)-Asp-Lys(Cbz)-Dab(Cbz)-aThr-Abu(2,3-dehydro)-Asp(3S-OH)-Thr(4-Cl)-(1) | 307498-26-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-Ser(1)-D-Dab(Cbz)-Asp-Lys(Cbz)-Dab(Cbz)-aThr-Abu(2,3-dehydro)-Asp(3S-OH)-Thr(4-Cl)-(1)
• 英文别名: (2S)-2-[(3S,6S,9Z,12S,15S,18S,21S,24R,27S)-27-amino-21-(carboxymethyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-9-ethylidene-12-[(1S)-1-hydroxyethyl]-2,5,8,11,14,17,20,23,26-nonaoxo-18-[4-(phenylmethoxycarbonylamino)butyl]-15,24-bis[2-(phenylmethoxycarbonylamino)ethyl]-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-hydroxyacetic acid
• CAS: 307498-26-6
• 化学式: C₆₁H₇₉ClN₁₂O₂₃
• 分子量: 1383.82
• InChiKey: JQOVBRZYACWRMZ-HBMUWTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  97
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  535
• 氢给体数：
  17
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxyoctadecanoic acid 、 H-Ser(1)-D-Dab(Cbz)-Asp-Lys(Cbz)-Dab(Cbz)-aThr-Abu(2,3-dehydro)-Asp(3S-OH)-Thr(4-Cl)-(1) 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  Syntheses and biological evaluation of novel pseudomycin side-chain analogues. Part 2

  摘要：

  A series of aliphatic side-chain analogues of pseudomycin was synthesized and evaluated during the course of our sidechain SAR effort. We found that several of the pseudomycin side-chain analogues (e.g., 10) exhibited good in vitro activity against all three major fungi responsible for systemic fungal infections. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00424-8
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 H-Ser(1)-D-Dab(Cbz)-Asp-Lys(Cbz)-Dab(Cbz)-aThr-Abu(2,3-dehydro)-Asp(3S-OH)-Thr(4-Cl)-(1)
  参考文献：
  名称：

  The synthesis of pseudomycin C′ via a novel acid promoted side-chain deacylation of pseudomycin A

  摘要：

  The gamma hydroxyl present in the aliphatic side chain of the natural products pseudomycin A and C' provided a unique handle for the pH dependent side-chain deacylation. Low pH reaction conditions were used to cleave the side chain with minimal degradation of the peptide core. The pseudomycin nucleus intermediate obtained from the deacylation of pseudomycin A was pivotal in the synthesis of novel side-chain analogues. A practical synthesis of a minor fermentation factor pseudomycin C' and related analogues is reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00613-2

文献信息

• Syntheses and antifungal activity of pseudomycin side-chain analogues. Part 1
  作者：James Jamison、Stuart Levy、Xicheng Sun、Doug Zeckner、William Current、Mark Zweifel、Michael Rodriguez、William Turner、Shu-Hui Chen

  DOI：10.1016/s0960-894x(00)00423-6

  日期：2000.9

  We have described herein the syntheses of three novel series of aromatic ring containing pseudomycin side-chain analogues. Preliminary biological evaluations of these analogues clearly indicate that it is possible to synthesize rigid pseudomycin sidechain analogues without compromising in vitro antifungal activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of novel pseudomycin side-chain analogues. Part 3
  作者：Xicheng Sun、Yan-Zhi Zhang、Doug Zeckner、William Current、Shu-Hui Chen

  DOI：10.1016/s0960-894x(01)00627-8

  日期：2001.12

  To increase the therapeutic utility of C-18 side-chain bearing pseudomycin analogue 2, we prepared additional analogues and prodrugs of 2 containing further modifications at various positions within its core structure. Each of the newly synthesized derivatives (10-15) exhibited reduced tail vein toxicity relative to the parent compound. Some of the new pseudomycin derivatives (e.g., 14) also showed improved in vivo antifungal activity relative to its corresponding parent compound. (C) 2001 Elsevier Science Ltd. All rights reserved.