[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-3-oxopropyl] octanoate | 369647-38-1

• 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: [(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-3-oxopropyl] octanoate
• CAS: 369647-38-1
• 化学式: C₂₉H₄₅N₃O₇S
• 分子量: 579.758
• InChiKey: WRSARNBHKABPAV-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-3-oxopropyl] octanoate 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S)-2-[[(2S)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]-3-phenylmethoxypropanoyl]amino]-3-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-3-oxopropyl] octanoate
  参考文献：
  名称：

  Spiro(indoline-3,4′-piperidine) growth hormone secretagogues as ghrelin mimetics

  摘要：

  A series of small molecules derived from MK-0677, a potent synthetic GHS, mimicking the N-terminal Gly-Ser-O-(n-octanoyl)-L-Ser-Phe segment of ghrelin was synthesized and tested in a binding and in a functional assay measuring intracellular calcium elevation in HEK-293 cells expressing hCHSR1a. Replacement of Phe in this tetrapeptide with a spiro(indoline-3,4 '- piperidine) group, Gly-Ser with 2-aminoisobutyric acid, and O-(n-octanoyl)-L-Ser with O-benzyl-D-Ser provided synthetic GHS agonists with similar functional potency as ghrelin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00324-9
• 作为产物：
  描述：

  在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 [(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-3-oxopropyl] octanoate
  参考文献：
  名称：

  Spiro(indoline-3,4′-piperidine) growth hormone secretagogues as ghrelin mimetics

  摘要：

  A series of small molecules derived from MK-0677, a potent synthetic GHS, mimicking the N-terminal Gly-Ser-O-(n-octanoyl)-L-Ser-Phe segment of ghrelin was synthesized and tested in a binding and in a functional assay measuring intracellular calcium elevation in HEK-293 cells expressing hCHSR1a. Replacement of Phe in this tetrapeptide with a spiro(indoline-3,4 '- piperidine) group, Gly-Ser with 2-aminoisobutyric acid, and O-(n-octanoyl)-L-Ser with O-benzyl-D-Ser provided synthetic GHS agonists with similar functional potency as ghrelin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00324-9

文献信息

• Spiro(indoline-3,4′-piperidine) growth hormone secretagogues as ghrelin mimetics
  作者：Brenda L. Palucki、Scott D. Feighner、Sheng-Shung Pong、Karen Kulju McKee、Donna L. Hreniuk、Carina Tan、Andrew D. Howard、Lex H.Y. Van der Ploeg、Arthur A. Patchett、Ravi P. Nargund

  DOI：10.1016/s0960-894x(01)00324-9

  日期：2001.7

  A series of small molecules derived from MK-0677, a potent synthetic GHS, mimicking the N-terminal Gly-Ser-O-(n-octanoyl)-L-Ser-Phe segment of ghrelin was synthesized and tested in a binding and in a functional assay measuring intracellular calcium elevation in HEK-293 cells expressing hCHSR1a. Replacement of Phe in this tetrapeptide with a spiro(indoline-3,4 '- piperidine) group, Gly-Ser with 2-aminoisobutyric acid, and O-(n-octanoyl)-L-Ser with O-benzyl-D-Ser provided synthetic GHS agonists with similar functional potency as ghrelin. (C) 2001 Elsevier Science Ltd. All rights reserved.