N,N-bis(tert-butoxycarbonyl)-2-(4-hydroxyphenethyl)-1-(pent-4-yn-1-yl)guanidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N-bis(tert-butoxycarbonyl)-2-(4-hydroxyphenethyl)-1-(pent-4-yn-1-yl)guanidine
• 英文别名: tert-butyl N-[N'-[2-(4-hydroxyphenyl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-pent-4-ynylcarbamate
• 化学式: C₂₄H₃₅N₃O₅
• 分子量: 445.559
• InChiKey: LYVVOWKVLBLIJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-bis(tert-butoxycarbonyl)-2-(4-hydroxyphenethyl)-1-(pent-4-yn-1-yl)guanidine 在 盐酸 、 copper(I) iodide triethylphosphite 、 水 、 chloroamine-T 、 sodium iodide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.33h， 生成 (S)-((3-(1-(2-((2-carboxy-1-phenylethyl)amino)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)propyl)amino)((4-hydroxy-3-iodophenethyl)amino)methaniminium trifluoroacetate
  参考文献：
  名称：

  Radiosynthesis and micro-SPECT analysis of triazole-based RGD integrin ligands as non-peptide molecular imaging probes for angiogenesis

  摘要：

  Taking advantage of click chemistry, we synthesized triazole-containing RGD peptidomimetics capable of binding to alpha(v)beta(3) integrin with diverse potency, and selected I-125-labeled compounds proved to interact in vitro and in vivo with alpha(v)beta(3) integrin expressed by melanoma cells. Two I-125-compounds containing either 2-aminobenzimidazole or 2-aminopyridine groups as the arginine bioisostere with the capacity to selectively bind cells of highly expressing alpha(v)beta(3) melanoma xenografts were found using micro-SPECT imaging studies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.065
• 作为产物：
  描述：

  N,N'-bis-Boc-S-methyl-isothiourea 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 N,N-bis(tert-butoxycarbonyl)-2-(4-hydroxyphenethyl)-1-(pent-4-yn-1-yl)guanidine
  参考文献：
  名称：

  [EN] 1,2,3-TRIAZOLE-BASED PEPTIDOMIMETIC INTEGRIN INHIBITORS FOR THE DIAGNOSIS AND THERAPY OF TUMORS
  [FR] INHIBITEURS PEPTIDOMIMÉTIQUES DE L'INTÉGRINE À BASE DE 1,2,3 TRIAZOLE POUR LE DIAGNOSTIC ET LE TRAITEMENT DE TUMEURS

  摘要：

  本发明涉及具有1,2,3-三唑环的化合物领域，其化学式为(I)，并具有胍基和羧基或其同系物，通过Cu催化的“点击化学”制备，用于在血管生成受损的病理情况中的医疗诊断用途，例如肿瘤来源的病理条件、肿瘤转移、骨质疏松症和类风湿性关节炎。

  公开号：

  WO2011098603A1

文献信息

• 1,2,3-TRIAZOLE-BASED PEPTIDOMIMETIC INTEGRIN INHIBITORS FOR THE DIAGNOSIS AND THERAPY OF TUMORS
  申请人：Guarna Antonio

  公开号：US20130040964A1

  公开（公告）日：2013-02-14

  The present invention refers to the field of chemical compounds bearing a 1,2,3-triazole ring of formula (I) and possessing guanidino and carboxylic groups or their isosteres, their preparation by Cu-catalyzed “click-chemistry”, and medical-diagnostic use in pathologies where angiogenesis is altered, for example pathologic conditions of tumor origin, tumor metastasis, osteoporosis, and rheumatoid arthritis.

  本发明涉及具有化学化合物的领域，其具有1,2,3-三唑环的结构（I）并且具有胍基和羧基或其同分异构体，通过铜催化的“点击化学”方法制备这些化合物，并在血管生成异常的病理学中进行医学诊断使用，例如肿瘤起源的病理性状况、肿瘤转移、骨质疏松症和类风湿性关节炎。
• US8809338B2
  申请人：——

  公开号：US8809338B2

  公开（公告）日：2014-08-19
• [EN] 1,2,3-TRIAZOLE-BASED PEPTIDOMIMETIC INTEGRIN INHIBITORS FOR THE DIAGNOSIS AND THERAPY OF TUMORS<br/>[FR] INHIBITEURS PEPTIDOMIMÉTIQUES DE L'INTÉGRINE À BASE DE 1,2,3 TRIAZOLE POUR LE DIAGNOSTIC ET LE TRAITEMENT DE TUMEURS
  申请人：UNIV FIRENZE

  公开号：WO2011098603A1

  公开（公告）日：2011-08-18

  The present invention refers to the field of chemical compounds bearing a 1,2,3-triazole ring of formula (I) and possessing guanidino and carboxylic groups or their isosteres, their preparation by Cu-catalyzed "click-chemistry", and medical - diagnostic use in pathologies where angiogenesis is altered, for example pathologic conditions of tumor origin, tumor metastasis, osteoporosis, and rheumatoid arthritis.

  本发明涉及具有1,2,3-三唑环的化合物领域，其化学式为(I)，并具有胍基和羧基或其同系物，通过Cu催化的“点击化学”制备，用于在血管生成受损的病理情况中的医疗诊断用途，例如肿瘤来源的病理条件、肿瘤转移、骨质疏松症和类风湿性关节炎。
• Radiosynthesis and micro-SPECT analysis of triazole-based RGD integrin ligands as non-peptide molecular imaging probes for angiogenesis
  作者：Francesca Bianchini、Pierangelo Fabbrizzi、Gloria Menchi、Silvia Raspanti、Anna Bottoncetti、Alessandro Passeri、Elena Andreucci、Antonio Guarna、Lido Calorini、Alberto Pupi、Andrea Trabocchi

  DOI：10.1016/j.bmc.2014.12.065

  日期：2015.3

  Taking advantage of click chemistry, we synthesized triazole-containing RGD peptidomimetics capable of binding to alpha(v)beta(3) integrin with diverse potency, and selected I-125-labeled compounds proved to interact in vitro and in vivo with alpha(v)beta(3) integrin expressed by melanoma cells. Two I-125-compounds containing either 2-aminobenzimidazole or 2-aminopyridine groups as the arginine bioisostere with the capacity to selectively bind cells of highly expressing alpha(v)beta(3) melanoma xenografts were found using micro-SPECT imaging studies. (C) 2015 Elsevier Ltd. All rights reserved.