D-Hica-D-Val-Lac-OBn

• 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: D-Hica-D-Val-Lac-OBn
• 英文别名: [(2S)-1-oxo-1-phenylmethoxypropan-2-yl] (2R)-2-[[(2R)-2-hydroxy-4-methylpentanoyl]amino]-3-methylbutanoate
• 化学式: C₂₁H₃₁NO₆
• 分子量: 393.48
• InChiKey: XOFXOWMHNVZARL-CGTJXYLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-Hica-D-Val-Lac-OBn 在 4-二甲氨基吡啶 、 三(2-氨基乙基)胺 、 palladium on activated charcoal 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 Fmoc-[Val-D-Hica-D-Val-Lac]2-OBn
  参考文献：
  名称：

  Antineoplastic Agents. 600. From the South Pacific Ocean to the Silstatins

  摘要：

  The recent advances in the development of antibody and other drug conjugates for targeted cancer treatment have further increased the need for powerful cancer cell growth inhibitors. Toward that objective we have extended our earlier discovery of the remarkable anticancer bacillistatins 1 and 2 from Bacillus silvestris to SAR and other structural modifications such as availability of a free hydroxy group for antibody-drug conjugate (ADC) and other prodrug linkage. That direction has resulted in seven structural modifications designated silstatins 1-8 (7a, 8a, 8b, 14a, 15a, 15b, 18a, and 18b), where the exceptional cancer cell growth inhibition of some of them are in the range GI(50) 10(-3)-10(-4) mu M/mL. Silstatin 7 (18a) was converted to a glucuronic conjugate (28) that displayed an impressive reduction in toxicity during transport.

  DOI：

  10.1021/np501004h
• 作为产物：
  描述：

  (S)-(-)-乳酸苄酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 D-Hica-D-Val-Lac-OBn
  参考文献：
  名称：

  Antineoplastic Agents. 600. From the South Pacific Ocean to the Silstatins

  摘要：

  The recent advances in the development of antibody and other drug conjugates for targeted cancer treatment have further increased the need for powerful cancer cell growth inhibitors. Toward that objective we have extended our earlier discovery of the remarkable anticancer bacillistatins 1 and 2 from Bacillus silvestris to SAR and other structural modifications such as availability of a free hydroxy group for antibody-drug conjugate (ADC) and other prodrug linkage. That direction has resulted in seven structural modifications designated silstatins 1-8 (7a, 8a, 8b, 14a, 15a, 15b, 18a, and 18b), where the exceptional cancer cell growth inhibition of some of them are in the range GI(50) 10(-3)-10(-4) mu M/mL. Silstatin 7 (18a) was converted to a glucuronic conjugate (28) that displayed an impressive reduction in toxicity during transport.

  DOI：

  10.1021/np501004h

文献信息

• SILSTATIN COMPOUNDS
  申请人：Pettit George Robert

  公开号：US20180030095A1

  公开（公告）日：2018-02-01

  The present disclosure relates to Silstatin compounds, pharmaceutical compositions comprising such compounds, kits, and methods for using such compounds or pharmaceutical compositions.
• Antineoplastic Agents. 600. From the South Pacific Ocean to the Silstatins
  作者：George R. Pettit、Pablo M. Arce、Jean-Charles Chapuis、Christian B. Macdonald

  DOI：10.1021/np501004h

  日期：2015.3.27

  The recent advances in the development of antibody and other drug conjugates for targeted cancer treatment have further increased the need for powerful cancer cell growth inhibitors. Toward that objective we have extended our earlier discovery of the remarkable anticancer bacillistatins 1 and 2 from Bacillus silvestris to SAR and other structural modifications such as availability of a free hydroxy group for antibody-drug conjugate (ADC) and other prodrug linkage. That direction has resulted in seven structural modifications designated silstatins 1-8 (7a, 8a, 8b, 14a, 15a, 15b, 18a, and 18b), where the exceptional cancer cell growth inhibition of some of them are in the range GI(50) 10(-3)-10(-4) mu M/mL. Silstatin 7 (18a) was converted to a glucuronic conjugate (28) that displayed an impressive reduction in toxicity during transport.