O-(tert-butyl)-N-((4-nitrophenoxy)carbonyl)-L-threonine tert-butyl ester | 1202237-10-2

• 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: O-(tert-butyl)-N-((4-nitrophenoxy)carbonyl)-L-threonine tert-butyl ester
• 英文别名: (2S,3R)-tert-butyl3-(tert-butoxy)-2-(((4-nitrophenoxy)carbonyl)amino)butanoate；tert-butyl (2S,3R)-3-[(2-methylpropan-2-yl)oxy]-2-[(4-nitrophenoxy)carbonylamino]butanoate
• CAS: 1202237-10-2
• 化学式: C₁₉H₂₈N₂O₇
• 分子量: 396.441
• InChiKey: AXTREXSQFCCOLX-DOMZBBRYSA-N

物化性质

• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O-(tert-butyl)-N-((4-nitrophenoxy)carbonyl)-L-threonine tert-butyl ester 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-3-hydroxy-2-[[(1S)-1-(3-pyrazin-2-yl-1,2,4-oxadiazol-5-yl)but-3-ynyl]carbamoylamino]butanoic acid
  参考文献：
  名称：

  In Vitro Assessment of Putative PD-1/PD-L1 Inhibitors: Suggestions of an Alternative Mode of Action

  摘要：

  The programmed cell death protein 1 (PD-1) signaling axis is among the most important therapeutic targets in modern oncology. Aurigene Discovery Technologies Ltd. (Aurigene) has patented a series of peptidomimetic small molecules derived from the PD-1 protein sequence for use in targeting the interaction between PD-1 and its ligand, PD-L1. We evaluated three of Aurigenes most potent compounds in SPR binding assays. Our results showed that these compounds-each of which is known to be potently effective in a splenocyte recovery assay-do not directly inhibit the PD-1/PD-L1 interaction nor do they appear to bind to either of the constituent proteins, indicating that another mechanism is at play. As a result of these studies and upon consideration of structural features within the PD-1/PD-L1 complex, we hypothesize that the Aurigene molecules may interact with a currently unknown protein capable of regulating the PD-1 axis.

  DOI：

  10.1021/acsmedchemlett.9b00221
• 作为产物：
  描述：

  对硝基苯基氯甲酸酯 、 O-tert-butyl-L-threonine tert-butyl ester hydrochloride 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到O-(tert-butyl)-N-((4-nitrophenoxy)carbonyl)-L-threonine tert-butyl ester
  参考文献：
  名称：

  [EN] SYNTHESIS AND USE OF HETEROCYCLIC ANTIBACTERIAL AGENTS
  [FR] SYNTHÈSE ET UTILISATION D'AGENTS ANTIBACTÉRIENS HÉTÉROCYCLIQUES

  摘要：

  这项发明涉及以下式（I）的化合物；或其药学上可接受的盐、溶剂合物、酯或异构体，用于治疗由LpxC介导的疾病或症状。

  公开号：

  WO2009158369A1

文献信息

• [EN] UREA DERIVATIVES AS ANTIBACTERIAL AGENTS<br/>[FR] DÉRIVÉS D'URÉE EN TANT QU'AGENTS ANTIBACTÉRIENS
  申请人：SCHERING CORP

  公开号：WO2010017060A1

  公开（公告）日：2010-02-11

  This invention relates to compounds of the Formula (I):or a pharmaceutically acceptable salt, solvate, ester or isomer thereof, which is useful for the treatment of diseases or conditions mediated by LpxC.

  这项发明涉及以下化合物的结构（I）：或其药用盐、溶剂合物、酯或异构体，用于治疗由LpxC介导的疾病或症状。
• [EN] 3-SUBSTITUTED 1,3,4-OXADIAZOLE AND THIADIAZOLE COMPOUNDS AS IMMUNOMODULATORS<br/>[FR] COMPOSÉS DE 1,3,4-OXADIAZOLE ET THIADIAZOLE SUBSTITUÉS EN POSITION 3 UTILISÉS EN TANT QU'IMMUNOMODULATEURS
  申请人：AURIGENE DISCOVERY TECH LTD

  公开号：WO2016142894A1

  公开（公告）日：2016-09-15

  The present invention relates to 3-substituted 1,3,4-oxadiazole and thiadiazole compounds of formula (I) and their use to inhibit the programmed cell death 1 (PD-1) signaling pathway and/or for treatment of disorders by inhibiting an immunosuppressive signal induced by PD-1, PD-L1 or PD-L2. 5

  本发明涉及式(I)的3-取代1,3,4-噁二唑和噻二唑化合物，以及它们的用途，用于抑制程序性细胞死亡1（PD-1）信号通路和/或通过抑制PD-1、PD-L1或PD-L2诱导的免疫抑制信号治疗疾病。
• Design and synthesis of potent Gram-negative specific LpxC inhibitors
  作者：U. Faruk Mansoor、Dilrukshi Vitharana、Panduranga Adulla Reddy、Dayna L. Daubaras、Paul McNicholas、Peter Orth、Todd Black、M. Arshad Siddiqui

  DOI：10.1016/j.bmcl.2010.12.111

  日期：2011.2

  Antibiotic resistant hospital acquired infections are on the rise, creating an urgent need for novel bactericidal drugs. Enzymes involved in lipopolysaccharide (LPS) biosynthesis are attractive antibacterial targets since LPS is the major structural component of the outer membrane of Gram-negative bacteria. Lipid A is an essential hydrophobic anchor of LPS and the first committed step in lipid A biosynthesis is catalyzed by a unique zinc dependent metalloamidase, UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC). LpxC is an attractive Gram-negative only target that has been chemically validated by potent bactericidal hydroxamate inhibitors that work by coordination of the enzyme's catalytic zinc ion. An exploratory chemistry effort focused on expanding the SAR around hydroxamic acid zinc-binding 'warheads' lead to the identification of novel compounds with enzyme potency and antibacterial activity similar to CHIR-090. (c) 2010 Elsevier Ltd. All rights reserved.
• SYNTHESIS AND USE OF HETEROCYCLIC ANTIBACTERIAL AGENTS
  申请人：Reddy Panduranga Adulla P.

  公开号：US20110212078A1

  公开（公告）日：2011-09-01

  This invention relates to compounds of the following Formula (I); or a pharmaceutically acceptable salt, solvate, ester or isomer thereof, which is useful for the treatment of diseases or conditions mediated by LpxC.
• UREA DERIVATIVES AS ANTIBACTERIAL AGENTS
  申请人：Mansoor Umar Faruk

  公开号：US20110212080A1

  公开（公告）日：2011-09-01

  This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate, ester or isomer thereof, which is useful for the treatment of diseases or conditions mediated by LpxC.