methyl 2-({[(benzyloxy)carbonyl]amino}methyl)-5-methyl-1,3-oxazole-4-carboxylate | 182866-71-3

• 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: methyl 2-({[(benzyloxy)carbonyl]amino}methyl)-5-methyl-1,3-oxazole-4-carboxylate
• 英文别名: methyl 2-[(benzyloxycarbonylamino)methyl]-5-methyloxazole-4-carboxylate；methyl 5-methyl-2-(phenylmethoxycarbonylaminomethyl)-1,3-oxazole-4-carboxylate
• CAS: 182866-71-3
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: MTYHQXYEFCPBHN-UHFFFAOYSA-N

物化性质

• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-({[(benzyloxy)carbonyl]amino}methyl)-5-methyl-1,3-oxazole-4-carboxylate 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 乙醇 、 水 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 (12S,19S,29S)-9,12,19,23-tetramethyl-5-(phenylmethoxymethyl)-29-propan-2-yl-10,24-dioxa-17,34-dithia-6,13,20,27,30,35,36,37,38-nonazahexacyclo[30.2.1.18,11.115,18.122,25.02,7]octatriaconta-1(35),2(7),3,5,8,11(38),15,18(37),22,25(36),32-undecaene-14,21,28,31-tetrone
  参考文献：
  名称：

  The first synthesis of promothiocin A

  摘要：

  描述了天然存在的大环硫肽promothiocin A 1 的首次全合成。

  DOI：

  10.1039/a805762a
• 作为产物：
  描述：

  Ethoxycarbonyl 2-(phenylmethoxycarbonylamino)acetate 在 dirhodium tetraacetate ammonium hydroxide 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.25h， 生成 methyl 2-({[(benzyloxy)carbonyl]amino}methyl)-5-methyl-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of functionalised oxazoles and bis-oxazoles 1

  摘要：

  开发了一种合成恶唑（特别是从氨基酸衍生的非外消旋手性恶唑）的新方法。因此，在酰胺8和10存在下，钌(II)催化的重氮羰基化合物6和11的反应导致卡宾类似物区域选择性地插入酰胺N-H键，形成β-羰基酰胺9和12。使用三苯基膦-碘-三乙胺对酰胺9和12进行环脱水反应，得到功能化的恶唑7和13。恶唑13c和13f通过在酰胺15上进行第二次钌(II)催化的区域选择性N-H插入反应，然后进行环脱水反应，被转化为双恶唑17a和17b。

  DOI：

  10.1039/a704093h

文献信息

• Distamycin Analogues with Enhanced Lipophilicity:  Synthesis and Antimicrobial Activity
  作者：Abedawn I. Khalaf、Roger D. Waigh、Allan J. Drummond、Breffni Pringle、Ian McGroarty、Graham G. Skellern、Colin J. Suckling

  DOI：10.1021/jm031089x

  日期：2004.4.1

  Forty-eight heterocyclic amino acid trimers, analogues of distamycin, with a number of features that enhance lipophilicity are described. They contain alkyl or cycloalkyl groups larger than methyl; some are N-terminated by acetamide or methoxybenzamide and are C-terminated by dimethylaminopropyl or aliphatic heterocylic aminopropyl substituents. The ability of these compounds to bind principally to

  描述了四十八个杂环氨基酸三聚体，它是二霉素的类似物，具有许多增强亲脂性的特征。它们含有比甲基大的烷基或环烷基；一些被乙酰胺或甲氧基苯甲酰胺N端基，并且被二甲氨基丙基或脂族杂环甲基氨基丙基取代基C端基。使用毛细管区带电泳已经评估了这些化合物主要结合至DNA AT束的能力。几种化合物，特别是那些含有噻唑的化合物，显示出对关键生物如MRSA和白色念珠菌的显着抗菌活性。而且，这些化合物对几种哺乳动物细胞系具有低毒性。
• The first synthesis of promothiocin A
  作者：Christopher J. Moody、Mark C. Bagley

  DOI：10.1039/a805762a

  日期：——

  The first total synthesis of the naturally occurring macrocyclic thiopeptide promothiocin A 1 is described.

  描述了天然存在的大环硫肽promothiocin A 1 的首次全合成。
• SORTASE A INHIBITORS
  申请人：Jung Michael E.

  公开号：US20120149710A1

  公开（公告）日：2012-06-14

  Bacterial infections, including Methicillin resistant Staphylococcus aureus (MRSA) infections are a major health problem that has created a pressing need for new antibiotics. Pyridazinone, rhodanine, and pyrazolethione compounds effective inhibit the enzymatic activity of sortase A (srtA) found in gram positive bacteria are disclosed. A structure activity relationship (SAR) analysis led to the identification of several pyridazinone and pyrazolethione analogs that inhibit SrtA with IC 50 values in the sub-micromolar range. Compounds that inhibit the S. aureus SrtA sortase may function as potent anti-infective agents as this enzyme attaches virulence factors to the cell wall. Many of these molecules also inhibit the sortase enzyme from B. anthracis suggesting that they may be generalized sortase inhibitors. The novel compounds, compositions, uses, formulations, medicaments, articles of manufacture provide improved materials, uses, and treatments useful in combating infectious disorders.

  细菌感染，包括甲氧西林耐药金黄色葡萄球菌（MRSA）感染，是一个重大的健康问题，已经创造了对新抗生素的迫切需求。本文披露了吡啶并咪唑酮、罗丹宁和吡唑硫酮化合物，这些化合物有效抑制了革兰氏阳性细菌中的srtA酶活性。结构活性关系（SAR）分析导致了多个吡啶并咪唑酮和吡唑硫酮类似物的鉴定，这些类似物以亚微摩尔范围内的IC50值抑制SrtA。抑制S. aureus SrtA酶的化合物可能作为强效抗感染剂，因为该酶将毒力因子附着在细胞壁上。其中许多分子也抑制了B. anthracis的sortase酶，表明它们可能是广谱的sortase抑制剂。这些新型化合物、组合物、用途、配方、药品和制造品提供了改进的材料、用途和治疗，对于抗击传染性疾病非常有用。
• [EN] SORTASE A INHIBITORS<br/>[FR] INHIBITEURS DE LA SORTASE A
  申请人：UNIV CALIFORNIA

  公开号：WO2011028492A2

  公开（公告）日：2011-03-10

  Bacterial infections, including Methicillin resistant Staphylococcus aureus (MRSA) infections are a major health problem that has created a pressing need for new antibiotics. Pyridazinone, rhodanine, and pyrazolethione compounds effective inhibit the enzymatic activity of sortase A (srtA) found in gram positive bacteria are disclosed. A structure activity relationship (SAR) analysis led to the identification of several pyridazinone and pyrazolethione analogs that inhibit SrtA with IC50 values in the sub-micromolar range. Compounds that inhibit the S. aureus SrtA sortase may function as potent anti-infective agents as this enzyme attaches virulence factors to the cell wall. Many of these molecules also inhibit the sortase enzyme from B. anthracis suggesting that they may be generalized sortase inhibitors. The novel compounds, compositions, uses, formulations, medicaments, articles of manufacture provide improved materials, uses, and treatments useful in combating infectious disorders.
• Total Synthesis of the Thiopeptide Promothiocin A
  作者：Mark C. Bagley、Katherine E. Bashford、Claire L. Hesketh、Christopher J. Moody

  DOI：10.1021/ja994247b

  日期：2000.4.1

  The thiopeptide (or thiostrepton) antibiotics are a class of sulfur-containing highly modified cyclic peptides with interesting biological activity. Described herein is the total synthesis of the thiopeptide antibiotic promothiocin A, which utilizes a modified Bohlmann-Rahtz pyridine synthesis to establish the oxazolyl-thiazole-pyridine heterocyclic centerpiece of the antibiotic. The oxazole building blocks were obtained by a dirhodium(II)-catalyzed chemoselective carbenoid N-H insertion reaction followed by cyclodehydration, and the thiazoles by the Hantzsch reaction. Two different strategies for macrocyclization were successfully employed, with the dehydroalanine side chain of the natural product being introduced in the last steps of the synthesis.