(5S)-5-benzyloxycarbonylamino-2-piperidone | 183536-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S)-5-benzyloxycarbonylamino-2-piperidone
• 英文别名: benzyl N-[(3S)-6-oxopiperidin-3-yl]carbamate
• CAS: 183536-40-5
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: ZYJPZLTUUVYWAG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-5-benzyloxycarbonylamino-2-piperidone 在 正丁基锂 、 氨 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (5S)-5-benzyloxycarbonylamino-1-diaminophosphoryl-2-piperidone
  参考文献：
  名称：

  Synthesis and biological activity of sulphostin analogues, novel dipeptidyl peptidase IV inhibitors

  摘要：

  The structure of sulphostin (1). a novel dipeptidyl peptidase IV (DPP-IV) inhibitor, is consisted of three key functional groups, including a characteristic amino(sulfoamino)phosphinyl group, on a piperidine ring. To examine the relationship between its structure and the inhibitory activity against DPP-IV. various analogues were synthesized and their activities were investitlaied- These results indicated that all of the functional groups on the piperidine ring were crucial to the DPP-IV inhibitory activity of sulphostin. and that the sulfonic acid group, which constructed the amino(sulfoamino)phosphinyl group, contributed to the stability of the compound. Moreover, those functional groups should be adjoined on the piperidine ring for the inhibitory acivity. The size of the nitrogen-containing heterocyclic ring including piperidine appeared to scarcely affect the activity. In the present study, the sulfonic acid-deficient five-membered ring analogue 27a showed the strongest inhibitory activity (IC50 = 11 nM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.036
• 作为产物：
  描述：

  methyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium azide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 生成 (5S)-5-benzyloxycarbonylamino-2-piperidone
  参考文献：
  名称：

  Synthesis of Chiral Triamines and Diamines from Amino Acids

  摘要：

  选择性保护的 (2S)-1,2,6-三氨基己烷 4 是通过还原氨基酸、用叠氮基团取代羟基和选择性还原法从 L-赖氨酸中制备出来的。按照同样的方法，从 L-谷氨酸合成了带有第三个官能团的代二胺 11 和 13。

  DOI：

  10.1055/s-1996-4358

文献信息

• Synthesis and biological activity of sulphostin analogues, novel dipeptidyl peptidase IV inhibitors
  作者：Masatoshi Abe、Tetsuo Akiyama、Yōji Umezawa、Keiichiro Yamamoto、Masashi Nagai、Hiroko Yamazaki、Yuh-ichiro Ichikawa、Yasuhiko Muraoka

  DOI：10.1016/j.bmc.2004.10.036

  日期：2005.2

  The structure of sulphostin (1). a novel dipeptidyl peptidase IV (DPP-IV) inhibitor, is consisted of three key functional groups, including a characteristic amino(sulfoamino)phosphinyl group, on a piperidine ring. To examine the relationship between its structure and the inhibitory activity against DPP-IV. various analogues were synthesized and their activities were investitlaied- These results indicated that all of the functional groups on the piperidine ring were crucial to the DPP-IV inhibitory activity of sulphostin. and that the sulfonic acid group, which constructed the amino(sulfoamino)phosphinyl group, contributed to the stability of the compound. Moreover, those functional groups should be adjoined on the piperidine ring for the inhibitory acivity. The size of the nitrogen-containing heterocyclic ring including piperidine appeared to scarcely affect the activity. In the present study, the sulfonic acid-deficient five-membered ring analogue 27a showed the strongest inhibitory activity (IC50 = 11 nM). (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Chiral Triamines and Diamines from Amino Acids
  作者：George Kokotos、Theodoros Markidis、Violetta Constantinou-Kokotou

  DOI：10.1055/s-1996-4358

  日期：1996.10

  Selectively protected (2S)-1,2,6-triaminohexane 4 was prepared from L-lysine by reduction of the amino acid, replacement of the hydroxy group by an azido group and selective reduction. Following the same method vicinal diamines 11 and 13 bearing a third functional group were synthesized from L-glutamic acid.

  选择性保护的 (2S)-1,2,6-三氨基己烷 4 是通过还原氨基酸、用叠氮基团取代羟基和选择性还原法从 L-赖氨酸中制备出来的。按照同样的方法，从 L-谷氨酸合成了带有第三个官能团的代二胺 11 和 13。