N-(tert-butyloxycarbonyl)-D-phenylalanyl-D-leucine methyl ester | 83588-11-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butyloxycarbonyl)-D-phenylalanyl-D-leucine methyl ester
• 英文别名: Boc-D-Phe-D-Leu-OMe；methyl (2R)-4-methyl-2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoate
• CAS: 83588-11-8
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: NUKWPDXDMGXCBV-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-D-phenylalanyl-D-leucine methyl ester 在 甲醇 、 双氧水 、 lithium hydroxide 、 盐酸 、 sodium thiosulfate 作用下， 以 甲醇 、 水 为溶剂， 以98%的产率得到(2R)-4-methyl-2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoic acid
  参考文献：
  名称：

  Design and synthesis of Hsp90 inhibitors: Exploring the SAR of Sansalvamide A derivatives

  摘要：

  Utilizing the structure-activity relationship we have developed during the synthesis of the first two generations and mechanism of action studies that point to the interaction of these molecules with the key oncogenic protein Hsp90, we report here the design of 32 new Sansalvamide A derivatives and their synthesis. Our new structures, designed from previously reported potent compounds, were tested for cytotoxicity on the HCT116 colon cancer cell line, and their binding to the biological target was analyzed using computational studies involving blind docking of derivatives using Autodock. Further, we show new evidence that our molecules bind directly to Hsp90 and modulate Hsp90's binding with client proteins. Finally, we demonstrate that we have integrated good ADME properties into a new derivative. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.07.042
• 作为产物：
  描述：

  Boc-Phe-Leu-OMe 生成 N-(tert-butyloxycarbonyl)-D-phenylalanyl-D-leucine methyl ester
  参考文献：
  名称：

  HIRAYAMA, CHUICHI;IHARA, HIROTAKA;TANAKA, KATSUNORI, J. CHROMATOGR., 450,(1988) N 2, C. 271-276

  摘要：

  DOI：

文献信息

• [EN] METHOD FOR PREPARING PEPTIDE AMIDE COMPOUND AND INTERMEDIATE THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ AMIDE PEPTIDIQUE ET INTERMÉDIAIRE DE CELUI-CI<br/>[ZH] 一种肽酰胺类化合物及其中间体的制备方法
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2021047470A1

  公开（公告）日：2021-03-18

  一种式(N)所示肽酰胺类化合物及其中间体的制备方法，该方法反应条件温和，操作简单，反应产率高，产品纯度高，后处理方便，适合于工业化生产。
• Activation Method to Prepare a Highly Reactive Acylsulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis¹
  作者：Bradley J. Backes、Alex A. Virgilio、Jonathan A. Ellman

  DOI：10.1021/ja9535165

  日期：1996.1.1
• HIRAYAMA, CHUICHI;IHARA, HIROTAKA;TANAKA, KATSUNORI, J. CHROMATOGR., 450,(1988) N 2, C. 271-276
  作者：HIRAYAMA, CHUICHI、IHARA, HIROTAKA、TANAKA, KATSUNORI

  DOI：——

  日期：——
• Design and synthesis of Hsp90 inhibitors: Exploring the SAR of Sansalvamide A derivatives
  作者：Robert P. Sellers、Leslie D. Alexander、Victoria A. Johnson、Chun-Chieh Lin、Jeremiah Savage、Ricardo Corral、Jason Moss、Tim S. Slugocki、Erinprit K. Singh、Melinda R. Davis、Suchitra Ravula、Jamie E. Spicer、Jenna L. Oelrich、Andrea Thornquist、Chung-Mao Pan、Shelli R. McAlpine

  DOI：10.1016/j.bmc.2010.07.042

  日期：2010.9

  Utilizing the structure-activity relationship we have developed during the synthesis of the first two generations and mechanism of action studies that point to the interaction of these molecules with the key oncogenic protein Hsp90, we report here the design of 32 new Sansalvamide A derivatives and their synthesis. Our new structures, designed from previously reported potent compounds, were tested for cytotoxicity on the HCT116 colon cancer cell line, and their binding to the biological target was analyzed using computational studies involving blind docking of derivatives using Autodock. Further, we show new evidence that our molecules bind directly to Hsp90 and modulate Hsp90's binding with client proteins. Finally, we demonstrate that we have integrated good ADME properties into a new derivative. Published by Elsevier Ltd.