ethyl 2-(N-benzyloxycarbonylaminomethyl)-4-thiazolecarboxylate | 112159-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(N-benzyloxycarbonylaminomethyl)-4-thiazolecarboxylate
• 英文别名: Benzyloxycarbonylaminomethyl-4-ethoxycarbonyl-thiazole；ethyl 2-({[(benzyloxy)carbonyl]amino}methyl)-1,3-thiazole-4-carboxylate；ethyl 2-(phenylmethoxycarbonylaminomethyl)-1,3-thiazole-4-carboxylate
• CAS: 112159-27-0
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: JFQJDJCJOIRJSC-UHFFFAOYSA-N

物化性质

• 沸点：
  484.2±35.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(N-benzyloxycarbonylaminomethyl)-4-thiazolecarboxylate 在 氢溴酸 、 溶剂黄146 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-(氨基甲基)-1,3-噻唑-4-羧酸
  参考文献：
  名称：

  Polythiazole linkers as functional rigid connectors: a new RGD cyclopeptide with enhanced integrin selectivity

  摘要：

  聚噻唑氨基酸将线性肽夹紧，以生成环状衍生物，但生成的物质不仅仅是钉合肽，而是具有复杂的杂环基团，展现出其固有的相互作用集。作为概念验证，一个双噻唑基团已被接枝到RGD序列上，以提供一种新的cilengitide类似物，具有改善的整合素选择性和显著的体内抗血管生成活性。

  DOI：

  10.1039/c4sc00572d
• 作为产物：
  描述：

  N-苄氧羰基氨基乙腈 在 molecular sieve 、 硫化氢 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 25.0h， 生成 ethyl 2-(N-benzyloxycarbonylaminomethyl)-4-thiazolecarboxylate
  参考文献：
  名称：

  Amino Acids and Peptides; 59.¹Synthesis of Biologically Active Cyclopeptides; 9.²Synthesis of 16 Isomers of Dolastatin 3;³I. Synthesis of the 2-(1-aminoalkyl)-thiazole-4-carboxylic Acids

  摘要：

  本文介绍了具有光学活性的多拉他汀 3 结构单元 2-(1-氨基-3-氰丙基)-噻唑-4-羧酸的合成过程，这是全合成多拉他汀异构体的先决条件。

  DOI：

  10.1055/s-1987-27899

文献信息

• Total synthesis of nosiheptide. Synthesis of thiazole fragments
  作者：Karen Koerber-Plé、Georges Massiot

  DOI：10.1002/jhet.5570320436

  日期：1995.7

  The preparation of three new thiazole derivatives from natural products is described, as well as improvements in the synthesis of ethyl 2-aminomethyl-4-thiazolecarboxylate.

  描述了从天然产物中制备三种新的噻唑衍生物的方法，以及2-氨基甲基-4-噻唑羧酸乙酯的合成方面的改进。
• [EN] PYRIDINE COMPOUNDS AS INHIBITORS OF DIPEPTIDYL PEPTIDASE IV<br/>[FR] COMPOSES PYRIDINES UTILISES COMME INHIBITEURS DE DIPEPTIDYLE PEPTIDASE IV
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2005042488A1

  公开（公告）日：2005-05-12

  A compound represented by the formula wherein R1 and R2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R3 is an optionally substituted aromatic group; R4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式表示为其中R1和R2相同或不同，每个都是可选择取代的碳氢基团或可选择取代的羟基团；R3是可选择取代的芳香基团；R4是可选择取代的氨基团；L是二价链状碳氢基团；Q是键或二价链状碳氢基团；X是氢原子、氰基、硝基、酰基、取代的羟基团、可选择取代的硫醇基团、可选择取代的氨基团或可选择取代的环状基团；但当X是乙氧羰基团时，Q为二价链状碳氢基团。该化合物具有肽酶抑制作用，可用作糖尿病等疾病的预防或治疗药物，并在功效、作用持续时间、特异性、毒性较低等方面具有优越性。
• SUBSTITUTED 1H-BENZIMIDAZOLE-4-CARBOXAMIDES ARE POTENT PARP INHIBITORS
  申请人：Penning D. Thomas

  公开号：US20070112047A1

  公开（公告）日：2007-05-17

  Compounds of Formula (I) inhibit the PARP enzyme and are useful for treating a disease or a disorder associated with PARP. Also disclosed are pharmaceutical compositions comprising compounds of Formula (I), methods of treatment comprising compounds of Formula (I), and methods of inhibiting the PARP enzyme comprising compounds of Formula (I).

  化合物的化学式(I)抑制PARP酶，可用于治疗与PARP相关的疾病或疾病。还披露了包含化合物的药物组合物的化学式(I)，包含化合物的治疗方法的方法的化学式(I)，以及包含化合物的PARP酶抑制方法的方法的化学式(I)。
• Azotides as Modular Peptide-Based Ligands for Asymmetric Lewis Acid Catalysis
  作者：Christian Borch Jacobsen、Daniel Steen Nielsen、Morten Meldal、Frederik Diness

  DOI：10.1021/acs.joc.9b00732

  日期：2019.6.7

  Synthesis of azotides and evaluation of these as ligands for enantioselective Lewis acid catalysis is reported. The ligands were readily prepared from the chiral pool of amino acids and perform well in the cobalt(II)-catalyzed formation of asymmetric hetero Diels–Alder adducts. A rational for the observed enantioselectivity and conversion rate supported by computational calculations is provided.

  据报道，偶氮化物的合成及其作为对映选择性路易斯酸催化的配体的评估。配体很容易从氨基酸的手性库中制备，并在钴（II）催化的不对称杂Diels-Alder加合物的形成中表现出色。提供了由计算计算支持的观察到的对映选择性和转化率的合理性。
• Pyridine compounds as inhibitors of dipeptidyl peptidase IV
  申请人：Oi Satoru

  公开号：US20070037807A1

  公开（公告）日：2007-02-15

  A compound represented by the formula wherein R 1 and R 2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R 3 is an optionally substituted aromatic group; R 4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式为其中R1和R2是相同或不同的可选择取代的烃基或可选择取代的羟基；R3是可选择取代的芳香基；R4是可选择取代的氨基；L是二价链烃基；Q是键或二价链烃基；X是氢原子、氰基、硝基、酰基、可选择取代的羟基、可选择取代的硫醇基、可选择取代的氨基或可选择取代的环状基；但当X是乙氧羰基时，Q是二价链烃基。该化合物具有肽酶抑制作用，可用作预防或治疗糖尿病等药物，具有优异的疗效、持续时间、特异性、低毒性等特点。