2-chloro-1-[6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-ethaneone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-chloro-1-[6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-ethaneone
• 英文别名: 2-chloro-1-[6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-yl]-ethanone；1-(6-benzyl-3,3-dimethyl-2H-pyrrolo[3,2-b]pyridin-1-yl)-2-chloroethanone
• 化学式: C₁₈H₁₉ClN₂O
• 分子量: 314.815
• InChiKey: XWYUSEWCDADOIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-[6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-ethaneone 、 (2R,5S)-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2R,5S)-4-[2-(6-benzyl-3,3-dimethyl-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl)-2-oxoethyl]-2-methyl-5-(2-oxopyrrolidin-1-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of a Potent Nonpeptidomimetic, Small-Molecule Antagonist of Cellular Inhibitor of Apoptosis Protein 1 (cIAP1) and X-Linked Inhibitor of Apoptosis Protein (XIAP)

  摘要：

  XIAP and cIAP1 are members of the inhibitor of apoptosis protein (IAP) family and are key regulators of anti-apoptotic and pro-survival signaling pathways. Over expression Of IAPs occurs in various cancers and has been associated with tumor progression and resistance to treatment. Structure-based drug design (SBDD) guided by structural information from X-ray crystallography, computational studies, and NMR solution conformational analysis was successfully applied to.a fragment-derived lead resulting, in AT-IAP, a potent, orally bioavailable, dual antagonist of XIAP and cIAP1 and a structurally novel chemical probe for LAP biology.

  DOI：

  10.1021/acs.jmedchem.6b01877
• 作为产物：
  描述：

  6-benzyl-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine hydrochloride 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-chloro-1-[6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-ethaneone
  参考文献：
  名称：

  Discovery of a Potent Nonpeptidomimetic, Small-Molecule Antagonist of Cellular Inhibitor of Apoptosis Protein 1 (cIAP1) and X-Linked Inhibitor of Apoptosis Protein (XIAP)

  摘要：

  XIAP and cIAP1 are members of the inhibitor of apoptosis protein (IAP) family and are key regulators of anti-apoptotic and pro-survival signaling pathways. Over expression Of IAPs occurs in various cancers and has been associated with tumor progression and resistance to treatment. Structure-based drug design (SBDD) guided by structural information from X-ray crystallography, computational studies, and NMR solution conformational analysis was successfully applied to.a fragment-derived lead resulting, in AT-IAP, a potent, orally bioavailable, dual antagonist of XIAP and cIAP1 and a structurally novel chemical probe for LAP biology.

  DOI：

  10.1021/acs.jmedchem.6b01877

文献信息

• [EN] BICYCLIC HETEROCYCLE COMPOUNDS AND THEIR USES IN THERAPY<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2014060770A1

  公开（公告）日：2014-04-24

  The invention relates to new bicyclic heterocycle compounds of formula (I):,to pharmaceutical compositions comprising said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

  该发明涉及公式(I)的新的双环杂环化合物，涉及包含该化合物的药物组合物，并涉及该化合物在治疗疾病（如癌症）中的用途。
• BICYCLIC HETEROCYCLE COMPOUNDS AND THEIR USES IN THERAPY
  申请人：ASTEX THERAPEUTICS LIMITED

  公开号：US20150353537A1

  公开（公告）日：2015-12-10

  The invention relates to new bicyclic heterocycle compounds, to pharmaceutical compositions comprising said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

  本发明涉及新的双环杂环化合物，以及包含该化合物的制药组合物，以及该化合物在治疗疾病（例如癌症）中的应用。
• US9617248B2
  申请人：——

  公开号：US9617248B2

  公开（公告）日：2017-04-11
• US9980973B2
  申请人：——

  公开号：US9980973B2

  公开（公告）日：2018-05-29
• Discovery of a Potent Nonpeptidomimetic, Small-Molecule Antagonist of Cellular Inhibitor of Apoptosis Protein 1 (cIAP1) and X-Linked Inhibitor of Apoptosis Protein (XIAP)
  作者：Emiliano Tamanini、Ildiko M. Buck、Gianni Chessari、Elisabetta Chiarparin、James E. H. Day、Martyn Frederickson、Charlotte M. Griffiths-Jones、Keisha Hearn、Tom D. Heightman、Aman Iqbal、Christopher N. Johnson、Edward J. Lewis、Vanessa Martins、Torren Peakman、Michael Reader、Sharna J. Rich、George A. Ward、Pamela A. Williams、Nicola E. Wilsher

  DOI：10.1021/acs.jmedchem.6b01877

  日期：2017.6.8

  XIAP and cIAP1 are members of the inhibitor of apoptosis protein (IAP) family and are key regulators of anti-apoptotic and pro-survival signaling pathways. Over expression Of IAPs occurs in various cancers and has been associated with tumor progression and resistance to treatment. Structure-based drug design (SBDD) guided by structural information from X-ray crystallography, computational studies, and NMR solution conformational analysis was successfully applied to.a fragment-derived lead resulting, in AT-IAP, a potent, orally bioavailable, dual antagonist of XIAP and cIAP1 and a structurally novel chemical probe for LAP biology.