benzyl L-pipecolyl-D-lactate | 187851-82-7

• 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: benzyl L-pipecolyl-D-lactate
• 英文别名: [(2R)-1-oxo-1-phenylmethoxypropan-2-yl] (2S)-piperidine-2-carboxylate
• CAS: 187851-82-7
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: CQQPQCPOJOYIJT-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl L-pipecolyl-D-lactate 在 10% palladium on active carbon 4-二甲氨基吡啶 、 氢气 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 33.0h， 生成
  参考文献：
  名称：

  Generation of a small library of cyclodepsipeptide PF1022A analogues using a cyclization-Cleavage method with oxime resin

  摘要：

  N-Methyloctadepsipeptides attached to an oxime resin were cyclized by heating them in refluxing ethyl acetate for 2 days to give cyclodepsipeptide PF1022A analogues. By using this method, we generated a small library of PF 1022A analogues (2), several of which possessed anthelmintic activity, based on an in vitro assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00748-x
• 作为产物：
  描述：

  N-Boc-L-哌啶-2-羧酸 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 benzyl L-pipecolyl-D-lactate
  参考文献：
  名称：

  Generation of a small library of cyclodepsipeptide PF1022A analogues using a cyclization-Cleavage method with oxime resin

  摘要：

  N-Methyloctadepsipeptides attached to an oxime resin were cyclized by heating them in refluxing ethyl acetate for 2 days to give cyclodepsipeptide PF1022A analogues. By using this method, we generated a small library of PF 1022A analogues (2), several of which possessed anthelmintic activity, based on an in vitro assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00748-x

文献信息

• Solid-phase synthesis of cyclooctadepsipeptide PF1022A analogs using a cyclization-cleavage method with oxime resin
  作者：Byung H. Lee

  DOI：10.1016/s0040-4039(96)02454-9

  日期：1997.2

  N-Methyloctadepsipeptides attached to an oxime resin were cyclized by heating them in refluxing ethyl acetate for 2 days to give cyclooctadepsipeptide PF1022A analogs.

  通过在回流的乙酸乙酯中加热它们使与肟树脂连接的N-甲基八肽肽环化2天，从而得到环八肽肽PF1022A类似物。
• Restricted Conformation Analogues of an Anthelmintic Cyclodepsipeptide
  作者：Fred E. Dutton、Byung H. Lee、Sandra S. Johnson、Eileen M. Coscarelli、Pil H. Lee

  DOI：10.1021/jm020482k

  日期：2003.5.1

  Six analogues of the anthelmintic cyclodepsipeptide PF1022A were prepared, each containing a small ring fused to the macrocycle to restrict the number of conformations the larger ring can adopt. It was anticipated that such conformational changes could lead to enhanced biological activity and selectivity. The analogues form two series of three members each. In one series, a carbon-based molecular bridge joins the methyl of a leucine residue with the methyl of its closest lactic acid residue to form five-, six-, and seven-membered lactam rings. In the second series, a leucine residue is replaced with five-, six-, and seven-membered nitrogen heterocycles. Decreasing the size of the small ring in the lactam. series increasingly distorts the macrocycle and consistently decreases activity relative to PF1022A. In the leucine series, a similar trend is observed. Molecular modeling of PF1022A along with the analogues described herein suggests that the ability to exist in a highly symmetrical conformational state is a necessary condition for biological activity.