(3aR,4aS,7R,8aR)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester | 851544-40-6

• 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: (3aR,4aS,7R,8aR)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3aR,4aS,7S,9aR)-1-benzyl-9-oxo-3,3a,4,4a,5,6,7,9a-octahydro-[1,2]oxazolo[3,4-f]indolizine-7-carboxylate
• CAS: 851544-40-6
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: WCGJTBGBRCOAEU-XLAORIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4aS,7R,8aR)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester 在 samarium diiodide 、 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.83h， 以68%的产率得到(3R,4R,6S,9S)-3-benzylamino-1-aza-2-oxo-4-hydroxymethyl-bicyclo[4.3.0]nonanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683
• 作为产物：
  描述：

  (2R,5R)-5-allyl-1-methoxyoxalylpyrrolidine-2-carboxylic acid tert-butyl ester 在 锂硼氢 、 草酰氯 、 碳酸氢钠 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (3aR,4aS,7R,8aR)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683

文献信息

• [EN] PEPTIDOMIMETIC COMPOUNDS, STEREOSELECTIVE PROCESS FOR THEIR PREPARATION, THEIR USE AS BIOLOGICALLY ACTIVE SYNTHETIC INTERMEDIATES<br/>[FR] COMPOSES PEPTIDOMIMETIQUES, LEUR PROCEDE STEREOSELECTIF DE PREPARATION, ET LEURS APPLICATIONS COMME INTERMEDIAIRES DE SYNTHESE A ACTIVITE BIOLOGIQUE
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2005042531A1

  公开（公告）日：2005-05-12

  The invention relates to novel cyclic peptidomimetic compounds having an azabicycloalkane structure, useful as intermediates in the preparation of αVΒ3 and αVΒ5 integrin antagonists, intended, for example, for the treatment of altered angiogenic phenomena; the invention also concerns a process for the stereoselective synthesis of said cyclic peptidomimetic compounds and biologically active derivatives thereof. Formula (I) wherein: n is 1 or 2, R1 is H, (C1-C4)alkyl,benzyl or a protective group; R2 is H or a protective group; R3 is H or heteroalkyl or a protective group; Their salts, racemic mixtures,individual enantiomers ,individual diastereoisomers and mixtures thereof in any proportion.

  该发明涉及具有氮杂环辛烷结构的新型环肽类似物化合物，可作为制备αVΒ3和αVΒ5整合素拮抗剂的中间体，例如用于治疗改变的血管生成现象；该发明还涉及一种用于立体选择性合成所述环肽类似物化合物及其生物活性衍生物的方法。公式（I）中：n为1或2，R1为H，（C1-C4）烷基，苄基或保护基；R2为H或保护基；R3为H或杂原子烷基或保护基；它们的盐，消旋混合物，单对映体，单顺异构体及其以任何比例混合。
• Improved synthesis of DA364, an NIR fluorescence RGD probe targeting α_vβ₃ integrin
  作者：Rachele Maschio、Federica Buonsanti、Federico Crivellin、Fulvio Ferretti、Luciano Lattuada、Federico Maisano、Laura Orio、Lorena Pizzuto、Raphael Campanella、Anthony Clouet、Camilla Cavallotti、Giovanni B. Giovenzana

  DOI：10.1039/d3ob01206a

  日期：——

  important class of fluorescent molecules and by their conjugation to peptides it is possible to achieve optical imaging of tumours by selective targeting. We report here the improvements obtained in the synthesis of DA364, a small fluorescent probe (1.5 kDa) prepared by conjugation of pentamethine cyanine Cy5.5 to an RGD peptidomimetic, which can target tumour cells overexpressing integrin αvβ3 receptors.

  光学成像 (OI) 作为一种非侵入性诊断成像技术和图像引导手术的有用工具，在医学领域越来越受到关注。OI 利用能够穿透活体组织的荧光分子在近红外区域发出的光。花青是一类重要的荧光分子，通过它们与肽的结合，可以通过选择性靶向来实现肿瘤的光学成像。我们在此报告了DA364合成中获得的改进，DA364 是一种小荧光探针 (1.5 kDA)，通过将五次甲基花青 Cy5.5 与 RGD 拟肽缀合而制备，可靶向过度表达整合素 α v β 3受体的肿瘤细胞。
• Peptidomimetic Compounds and Preparation of Biologically Active Derivatives
  申请人：Scolastico Carlo

  公开号：US20080139461A1

  公开（公告）日：2008-06-12

  The invention relates to novel cyclic peptidomimetic compounds containing the sequence RGD for the preparation of appropriately functionalised antagonists of αvβ3 and αvβ5 integrins, and intended, for example, for the treatment of altered angiogenic phenomena or for the preparation of diagnostically useful compounds.