methyl (2R)-3-hydroxy-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]propanoate | 179053-09-9

• 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: methyl (2R)-3-hydroxy-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]propanoate
• CAS: 179053-09-9
• 化学式: C₁₁H₂₂N₂O₅
• 分子量: 262.306
• InChiKey: UZZOVMULLXBEMS-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R)-3-hydroxy-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]propanoate 在 盐酸 、 甲醇 、 10% palladium on activated charcoal 、 氢气 、 三甲基铝 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 生成 (3R)-3-(Hydroxymethyl)piperazin-2-one
  参考文献：
  名称：

  Discovery of DA-1229: A potent, long acting dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes

  摘要：

  A series of beta-amino amide containing substituted piperazine-2-one derivatives was synthesized and evaluated as inhibitors of dipeptidyl pepdidase-4 (DPP-4) for the treatment of type 2 diabetes. As results of intensive SAR study of the series, (R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butanoyl]-3-(t-butoxymethyl)-piperazin-2-one (DA-1229) displayed potent DPP-4 inhibition pattern in several animal models, was selected for clinical development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.029
• 作为产物：
  描述：

  D-丝氨酸甲酯 、 N-叔丁氧羰基-2-氨基乙醛 在 三乙酰氧基硼氢化钠 作用下， 生成 methyl (2R)-3-hydroxy-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]propanoate
  参考文献：
  名称：

  Discovery of DA-1229: A potent, long acting dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes

  摘要：

  A series of beta-amino amide containing substituted piperazine-2-one derivatives was synthesized and evaluated as inhibitors of dipeptidyl pepdidase-4 (DPP-4) for the treatment of type 2 diabetes. As results of intensive SAR study of the series, (R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butanoyl]-3-(t-butoxymethyl)-piperazin-2-one (DA-1229) displayed potent DPP-4 inhibition pattern in several animal models, was selected for clinical development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.029

文献信息

• PEPTIDE NUCLEIC ACID CONJUGATES
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0804456B1

  公开（公告）日：2002-08-21
• EP0804456A4
  申请人：——

  公开号：EP0804456A4

  公开（公告）日：1999-05-19
• US7223833B1
  申请人：——

  公开号：US7223833B1

  公开（公告）日：2007-05-29
• [EN] PEPTIDE NUCLEIC ACID CONJUGATES<br/>[FR] CONJUGUES D'ACIDES NUCLEIQUES PEPTIDIQUES
  申请人：——

  公开号：WO1996011205A1

  公开（公告）日：1996-04-18

  [EN] A novel class of peptide nucleic acids are described which include a conjugate attached thereto. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.
  [FR] Cette invention se rapporte à un nouvelle classe d'acides nucléiques peptidiques, qui contiennent un conjugué fixé à eux. Ces acides nucléiques peptidiques comprennent généralement des ligands tels que des bases d'ADN existant à l'état naturel, qui sont fixées à un squelette peptidique par un segment de liaison approprié.
• Discovery of DA-1229: A potent, long acting dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes
  作者：Heung Jae Kim、Woo Young Kwak、Jong Pil Min、Jae Young Lee、Tae Hyun Yoon、Ha Dong Kim、Chang Yell Shin、Mi Kyung Kim、Song Hyen Choi、Hae Sun Kim、Eun Kyoung Yang、Ye Hwang Cheong、Yu Na Chae、Kyung Jin Park、Ji Myun Jang、Soo Jung Choi、Moon Ho Son、Soon Hoe Kim、Moohi Yoo、Bong Jin Lee

  DOI：10.1016/j.bmcl.2011.04.029

  日期：2011.6

  A series of beta-amino amide containing substituted piperazine-2-one derivatives was synthesized and evaluated as inhibitors of dipeptidyl pepdidase-4 (DPP-4) for the treatment of type 2 diabetes. As results of intensive SAR study of the series, (R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butanoyl]-3-(t-butoxymethyl)-piperazin-2-one (DA-1229) displayed potent DPP-4 inhibition pattern in several animal models, was selected for clinical development. (C) 2011 Elsevier Ltd. All rights reserved.