[5-(benzyloxycarbonyl)amino-5-(N-methoxy-N-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester | 172833-41-9

• 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: [5-(benzyloxycarbonyl)amino-5-(N-methoxy-N-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester
• 英文别名: benzyl tert-butyl (6-(methoxy(methyl)amino)-6-oxohexane-1,5-diyl)(S)-dicarbamate
• CAS: 172833-41-9
• 化学式: C₂₁H₃₃N₃O₆
• 分子量: 423.51
• InChiKey: WBYSPJINWNELOS-KRWDZBQOSA-N

物化性质

• 密度：
  1.136±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  106.2
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [5-(benzyloxycarbonyl)amino-5-(N-methoxy-N-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 氢气 、 羟胺 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 [5-amino-6-{5-[4-(3,4-dichlorophenethyloxy)phenylmethyl]-[1,2,4]oxadiazol-3-yl}-6-(tert-butyl-dimethylsilyloxy)-hexyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of selective keto-1,2,4-oxadiazole-based tryptase inhibitors

  摘要：

  Using a scaleable, directed library approach based on orthogonally protected advanced intermediates, we have prepared a series of potent keto-1,2,4-oxadiazoles designed to explore the P-2 binding pocket of human mast cell tryptase, while building in a high degree of selectivity over human trypsin and other serine proteases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.013
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 在 TEA 作用下， 生成 [5-(benzyloxycarbonyl)amino-5-(N-methoxy-N-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Fantetti, Lia; Adembri, Giorgio; Giotti, Alberto, Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 2, p. 137 - 143

  摘要：

  DOI：

文献信息

• Design of novel, potent, and selective human β-tryptase inhibitors based on α-keto-[1,2,4]-oxadiazoles
  作者：Chang-Sun Lee、Weili Liu、Paul A. Sprengeler、John R. Somoza、James W. Janc、David Sperandio、Jeffrey R. Spencer、Michael J. Green、Mary E. McGrath

  DOI：10.1016/j.bmcl.2006.05.009

  日期：2006.8

  A series of novel alpha-keto-[1,2,4]-oxadiazoles has been synthesized as human tryptase inhibitors for evaluation as a new class of anti-asthmatic agent. The inhibitor design is focused on using a prime-side hydrophobic pocket and the S2 pocket of beta-tryptase to achieve inhibition potency and selectivity over other serine proteases.

  已经合成了一系列新型的α-酮-[1,2,4]-恶二唑类化合物作为人类类胰蛋白酶抑制剂，作为一类新型的抗哮喘药进行评估。抑制剂的设计着眼于使用β-胰蛋白酶的素侧疏水袋和S2袋，以实现对其他丝氨酸蛋白酶的抑制效力和选择性。
• WO2006/44133
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel, potent, selective, and orally bioavailable human βII-tryptase inhibitors
  作者：David Sperandio、Vincent W.-F. Tai、Julia Lohman、Bernie Hirschbein、Rohan Mendonca、Chang-Sun Lee、Jeffrey R. Spencer、James Janc、Margaret Nguyen、Jerlyn Beltman、Paul Sprengeler、Heleen Scheerens、Tong Lin、Liang Liu、Ashwini Gadre、Alisha Kellogg、Michael J. Green、Mary E. McGrath

  DOI：10.1016/j.bmcl.2006.04.088

  日期：2006.8

  The synthesis of novel [1,2,4]oxadiazoles and their structure-activity relationship (SAR) for the inhibition of tryptase and related serine proteases is presented. Elaboration of the P'-side afforded potent, selective, and orally bioavailable tryptase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.
• Dynamics Determine Signaling in a Multicomponent System Associated with Rheumatoid Arthritis
  作者：Cecilia Lindgren、Mohit Tyagi、Johan Viljanen、Johannes Toms、Changrong Ge、Naru Zhang、Rikard Holmdahl、Jan Kihlberg、Anna Linusson

  DOI：10.1021/acs.jmedchem.7b01880

  日期：2018.6.14

  Strategies that target multiple components are usually required for treatment of diseases originating from complex biological systems. The multicomponent system consisting of the DR4 major histocompatibility complex type II molecule, the glycopeptide CI1259-273 from type II collagen, and a T-cell receptor is associated with development of rheumatoid arthritis (RA). We introduced non-native amino acids and amide bond isosteres into CI1259-273 and investigated the effect on binding to DR4 and the subsequent T-cell response. Molecular dynamics simulations revealed that complexes between DR4 and derivatives of CI1259-273 were highly dynamic. Signaling in the overall multicomponent system was found to depend on formation of an appropriate number of dynamic intramolecular hydrogen bonds between DR4 and CI1259-273, together with the positioning of the galactose moiety of CI1259-273 in the DR4 binding groove. Interestingly, the system tolerated modifications at several positions in CI1259-273, indicating opportunities to use analogues to increase our understanding of how rheumatoid arthritis develops and for evaluation as vaccines to treat RA.
• [EN] PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉASE
  申请人：[en]PROTINHI B.V.

  公开号：WO2023052636A1

  公开（公告）日：2023-04-06

  The present invention relates to a new class of compounds based on alkylated oligopeptides featuring distinct head and tail modifications at their termini. The compounds are useful as inhibitors of viral proteases, particularly of flaviviral proteases, and can therefore be used for treatment of viral infections.