tert-butyl N-[(1S)-1-[5-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-1,3,4-oxadiazol-2-yl]-2-(1H-indol-3-yl)ethyl]carbamate | 1007872-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl N-[(1S)-1-[5-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-1,3,4-oxadiazol-2-yl]-2-(1H-indol-3-yl)ethyl]carbamate
• CAS: 1007872-54-9
• 化学式: C₂₇H₃₁N₅O₄S
• 分子量: 521.64
• InChiKey: KXYDQYFULDQFLV-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-[5-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-1,3,4-oxadiazol-2-yl]-2-(1H-indol-3-yl)ethyl]carbamate 在 三氟乙酸 作用下， 反应 0.25h， 以89%的产率得到2-[[5-[(1S)-1-amino-2-(1H-indol-3-yl)ethyl]-1,3,4-oxadiazol-2-yl]sulfanyl]-N-(2-ethylphenyl)acetamide;hydrochloride
  参考文献：
  名称：

  Identification and synthesis of a unique thiocarbazate cathepsin L inhibitor

  摘要：

  Library samples containing 2,5-disubstituted oxadiazoles were identified as potent hits in a high throughput screen (HTS) of the NIH Molecular Libraries Small Molecule Repository (MLSMR) directed at discovering inhibitors of cathepsin L. However, when synthesized in pure form, the putative actives were found to be devoid of biological activity. Analyses by LC-MS of original library samples indicated the presence of a number of impurities, in addition to the oxadiazoles. Synthesis and bioassay of the probable impurities led to the identification of a thiocarbazate that likely originated via ring opening of the oxadiazole. Previously unknown, thiocarbazates (-)-11 and (-)-12 were independently synthesized as single enantiomers and found to inhibit cathepsin L in the low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.107
• 作为产物：
  描述：

  2-溴-N-(2-乙基苯基)乙酰胺 、 tert-butyl N-[(1S)-2-(1H-indol-3-yl)-1-(2-sulfanylidene-3H-1,3,4-oxadiazol-5-yl)ethyl]carbamate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以94%的产率得到tert-butyl N-[(1S)-1-[5-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-1,3,4-oxadiazol-2-yl]-2-(1H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  Identification and synthesis of a unique thiocarbazate cathepsin L inhibitor

  摘要：

  Library samples containing 2,5-disubstituted oxadiazoles were identified as potent hits in a high throughput screen (HTS) of the NIH Molecular Libraries Small Molecule Repository (MLSMR) directed at discovering inhibitors of cathepsin L. However, when synthesized in pure form, the putative actives were found to be devoid of biological activity. Analyses by LC-MS of original library samples indicated the presence of a number of impurities, in addition to the oxadiazoles. Synthesis and bioassay of the probable impurities led to the identification of a thiocarbazate that likely originated via ring opening of the oxadiazole. Previously unknown, thiocarbazates (-)-11 and (-)-12 were independently synthesized as single enantiomers and found to inhibit cathepsin L in the low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.107

文献信息

• Identification and synthesis of a unique thiocarbazate cathepsin L inhibitor
  作者：Michael C. Myers、Parag P. Shah、Scott L. Diamond、Donna M. Huryn、Amos B. Smith

  DOI：10.1016/j.bmcl.2007.10.107

  日期：2008.1

  Library samples containing 2,5-disubstituted oxadiazoles were identified as potent hits in a high throughput screen (HTS) of the NIH Molecular Libraries Small Molecule Repository (MLSMR) directed at discovering inhibitors of cathepsin L. However, when synthesized in pure form, the putative actives were found to be devoid of biological activity. Analyses by LC-MS of original library samples indicated the presence of a number of impurities, in addition to the oxadiazoles. Synthesis and bioassay of the probable impurities led to the identification of a thiocarbazate that likely originated via ring opening of the oxadiazole. Previously unknown, thiocarbazates (-)-11 and (-)-12 were independently synthesized as single enantiomers and found to inhibit cathepsin L in the low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.