3-NH2-phenyl sulfonyl-Phe(3-Boc-Ame)-4-(2-Boc-amidoethyl)piperidide | 1124182-54-2

• 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: 3-NH2-phenyl sulfonyl-Phe(3-Boc-Ame)-4-(2-Boc-amidoethyl)piperidide
• 英文别名: tert-butyl N-[[3-[(2S)-2-[(3-aminophenyl)sulfonylamino]-3-[4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]piperidin-1-yl]-3-oxopropyl]phenyl]methyl]carbamate
• CAS: 1124182-54-2
• 化学式: C₃₃H₄₉N₅O₇S
• 分子量: 659.847
• InChiKey: PKGQHOIKUCOOKW-NDEPHWFRSA-N

物化性质

• 密度：
  1.205±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-NH2-phenyl sulfonyl-Phe(3-Boc-Ame)-4-(2-Boc-amidoethyl)piperidide 、 Boc-beta-丙氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Modification of the N-terminal sulfonyl residue in 3-amidinophenylalanine-based matriptase inhibitors

  摘要：

  Replacement of the N-terminal beta-alanyl-amide moiety in previously identified matriptase inhibitors by non-charged aryl groups caused a slightly decreased potency and partially reduced selectivity, especially towards thrombin. However, some of these analogues are still potent matriptase inhibitors with K(i)-values <10 nM. In contrast, improved activity was observed for newly designed tribasic analogues, especially for compound 21, which inhibits matriptase with an K(i)-value of 80 pM. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.019
• 作为产物：
  描述：

  3-NH2-phenyl sulfonyl-Phe(3-Boc-Ame)-OH 、 4-(2-Boc-氨乙基)哌啶 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-NH2-phenyl sulfonyl-Phe(3-Boc-Ame)-4-(2-Boc-amidoethyl)piperidide
  参考文献：
  名称：

  META-SUBSTITUTED PHENYL SULFONYL AMIDES OF SECONDARY AMINO ACID AMIDES, THE PRODUCTION THEREOF, AND USE THEREOF AS MATRIPTASE INHIBITORS

  摘要：

  该发明涉及通式（I）、（II）或（III）的次级氨基酸酰胺的亚苯基磺酰胺，其制备方法以及其作为matriptase抑制剂的用途，特别是其作为抑制肿瘤生长和/或转移的药物的用途。

  公开号：

  US20100305090A1

文献信息

• META-SUBSTITUTED PHENYL SULFONYL AMIDES OF SECONDARY AMINO ACID AMIDES, THE PRODUCTION THEREOF, AND USE THEREOF AS MATRIPTASE INHIBITORS
  申请人：Steinmetzer Torsten

  公开号：US20100305090A1

  公开（公告）日：2010-12-02

  The invention relates to meta-substituted phenyl sulfonyl amides of secondary amino acid amides according to the general formula (I), (II), or (III), the production thereof, and the use thereof as matriptase inhibitors, in particular the use thereof as drugs for inhibiting tumor growth and/or metastasization.

  该发明涉及通式（I）、（II）或（III）的次级氨基酸酰胺的亚苯基磺酰胺，其制备方法以及其作为matriptase抑制剂的用途，特别是其作为抑制肿瘤生长和/或转移的药物的用途。
• META-SUBSTITUIERTE PHENYLSULFONYLAMIDE SEKUNDÄRER AMINOSÄUREAMIDE ALS HEMMSTOFFE DER MATRIPTASE ZUR HEMMUNG DES TUMORWACHSTUMS UND/ODER DER METASTASIERUNG VON TUMOREN
  申请人：The Medicines Company (Leipzig) GmbH

  公开号：EP2132174B1

  公开（公告）日：2012-02-01
• US8569313B2
  申请人：——

  公开号：US8569313B2

  公开（公告）日：2013-10-29
• [DE] META-SUBSTITUIERTE PHENYLSULFONYLAMIDE SEKUNDÄRER AMINOSÄUREAMIDE ALS HEMMSTOFFE DER MATRIPTASE ZUR HEMMUNG DES TUMORWACHSTUMS UND/ODER DER METASTASIERUNG VON TUMOREN<br/>[EN] META-SUBSTITUTED PHENYL SULFONYL AMIDES OF SECONDARY AMINO ACID AMIDES, THE PRODUCTION THEREOF, AND USE THEREOF AS MATRIPTASE INHIBITORS<br/>[FR] AMIDES D'AMINOACIDES SECONDAIRES DE PHÉNYLSULFONYLAMIDE MÉTA-SUBSTITUÉ, LEUR PRODUCTION ET LEUR UTILISATION COMME INHIBITEURS DE LA MATRIPTASE
  申请人：CURACYTE DISCOVERY GMBH

  公开号：WO2008107176A1

  公开（公告）日：2008-09-12

  [EN] The invention relates to meta-substituted phenyl sulfonyl amides of secondary amino acid amides according to the general formula (I), (II), or (III), the production thereof, and the use thereof as matriptase inhibitors, in particular the use thereof as drugs for inhibiting tumor growth and/or metastasization.
  [FR] L'invention concerne des amides d'aminoacides secondaires de phénylsulfonylamide méta-substitué, conformes à la formule générale (I), (II) ou (III), leur production et leur utilisation comme inhibiteurs de la matriptase, en particulier leur utilisation comme médicaments servant à inhiber la croissance tumorale et/ou la formation des métastases.
  [DE] Die Erfindung betrifft meta-substituierte Phenylsulfonylamide sekundärer Aminosäureamide gemäss der allgemeinen Formel (I), (II) oder (III), ihre Herstellung und Verwendung als Hemmstoffe der Matriptase, insbesondere deren Verwendung als Arzneimittel zur Hemmung des Tumorwachstums und/oder der Metastasierung.
• Modification of the N-terminal sulfonyl residue in 3-amidinophenylalanine-based matriptase inhibitors
  作者：Torsten Steinmetzer、Daniel Dönnecke、Martin Korsonewski、Claudia Neuwirth、Peter Steinmetzer、Alexander Schulze、Sebastian Martin Saupe、Andrea Schweinitz

  DOI：10.1016/j.bmcl.2008.11.019

  日期：2009.1

  Replacement of the N-terminal beta-alanyl-amide moiety in previously identified matriptase inhibitors by non-charged aryl groups caused a slightly decreased potency and partially reduced selectivity, especially towards thrombin. However, some of these analogues are still potent matriptase inhibitors with K(i)-values <10 nM. In contrast, improved activity was observed for newly designed tribasic analogues, especially for compound 21, which inhibits matriptase with an K(i)-value of 80 pM. (C) 2008 Elsevier Ltd. All rights reserved.