2-(N-9-fluorenylmethyloxycarbonyl)aminomethyl-2'-carboxymethyl-biphenyl | 957128-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(N-9-fluorenylmethyloxycarbonyl)aminomethyl-2'-carboxymethyl-biphenyl
• 英文别名: 2-(2'-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-[1,1'-biphenyl]-2-yl)acetic acid；2-[2-[2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]phenyl]phenyl]acetic acid
• CAS: 957128-13-1
• 化学式: C₃₀H₂₅NO₄
• 分子量: 463.533
• InChiKey: GWDJJYZHKGQOOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(N-9-fluorenylmethyloxycarbonyl)aminomethyl-2'-carboxymethyl-biphenyl 、 Fmoc-L-缬氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-Pbf-L-精氨酸 生成
  参考文献：
  名称：

  Biaryl amino acid templates in place of d-Pro-l-Pro in cyclic ß-hairpin cationic antimicrobial peptidomimetics

  摘要：

  转向形成的D-Pro-L-Pro模板常被用于促进环状蛋白表位模拟物中的规则β-发夹构象。这里研究了三种异构体的双芳基模板作为D-Pro-L-Pro的替代品，用于制备β-发夹肽模拟物。o,o'、o,m'和m,m'异构体的羧甲基和氨甲基取代的双芳基模板被引入到自然发生的阳离子抗菌肽protegrin I的新型宏环模拟物中。o-羧甲基-o'-氨甲基双芳基模板的存在使得宏环肽中出现了缓慢互变的厄尔托普异构体。尽管最终得到的模拟物在水溶液中未能形成稳定的β-发夹结构，它们仍保留了对革兰氏阳性和革兰氏阴性细菌的显著抗菌活性。这些模拟物为寻找强效和新型抗菌化合物的优化程序提供了有趣的出发点。

  DOI：

  10.1039/b706370a
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 2'-(aminomethyl)biphenyl-2-acetic acid 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以1.2 g的产率得到2-(N-9-fluorenylmethyloxycarbonyl)aminomethyl-2'-carboxymethyl-biphenyl
  参考文献：
  名称：

  Biaryl amino acid templates in place of d-Pro-l-Pro in cyclic ß-hairpin cationic antimicrobial peptidomimetics

  摘要：

  转向形成的D-Pro-L-Pro模板常被用于促进环状蛋白表位模拟物中的规则β-发夹构象。这里研究了三种异构体的双芳基模板作为D-Pro-L-Pro的替代品，用于制备β-发夹肽模拟物。o,o'、o,m'和m,m'异构体的羧甲基和氨甲基取代的双芳基模板被引入到自然发生的阳离子抗菌肽protegrin I的新型宏环模拟物中。o-羧甲基-o'-氨甲基双芳基模板的存在使得宏环肽中出现了缓慢互变的厄尔托普异构体。尽管最终得到的模拟物在水溶液中未能形成稳定的β-发夹结构，它们仍保留了对革兰氏阳性和革兰氏阴性细菌的显著抗菌活性。这些模拟物为寻找强效和新型抗菌化合物的优化程序提供了有趣的出发点。

  DOI：

  10.1039/b706370a

文献信息

• CYCLIC PEPTIDES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF THE PLATELET ADHESION
  申请人：SANOFI

  公开号：EP2598157B1

  公开（公告）日：2016-10-12
• US9073975B2
  申请人：——

  公开号：US9073975B2

  公开（公告）日：2015-07-07
• [EN] CYCLIC PEPTIDES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF THE PLATELET ADHESION<br/>[FR] PEPTIDES CYCLIQUES, LEUR PRÉPARATION ET LEUR UTILISATION COMME INHIBITEURS DE L'ADHÉSION DES PLAQUETTES
  申请人：SANOFI SA

  公开号：WO2012013709A1

  公开（公告）日：2012-02-02

  The present invention relates to compounds of the Formula (I), in which R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, X1, X2, X3 and X4 have the meanings indicated in the claims, and which are valuable pharmacologically active compounds. They are reversible inhibitors of the interaction between the plasma protein von Willebrand factor (vWF) and the blood platelet receptor glycoprotein Ib-IX-V complex (GPIb),and are suitable, for example, for the therapy and prophylaxis of athero-thrombotic diseases. The invention furthermore relates to processes for the preparation of compounds of the Formula (I), their use, in particular as active ingredients in medicaments, and pharmaceutical compositions comprising them.
• Biaryl amino acid templates in place of d-Pro-l-Pro in cyclic ß-hairpin cationic antimicrobial peptidomimetics
  作者：Nityakalyani Srinivas、Kerstin Moehle、Khaled Abou-Hadeed、Daniel Obrecht、John A. Robinson

  DOI：10.1039/b706370a

  日期：——

  The turn-forming D-Pro-L-Pro template has been frequently used to promote regular ß-hairpin conformations in cyclic protein epitope mimetics. Here the use of three isomeric biaryl templates has been studied as alternatives to D-Pro-L-Pro in the preparation of ß-hairpin peptidomimetics. The o,o′- o,m′- and m,m′-isomers of carboxymethyl- and aminomethyl-substituted biaryl templates have been incorporated into novel macrocyclic mimics of the naturally occurring cationic antimicrobial peptide protegrin I. The presence of the o-carboxymethyl-o′-aminomethyl-biaryl template within the macrocyclic peptide resulted in the appearance of slowly interconverting atropisomers. Although none of the resulting mimetics adopted stable ß-hairpin structures in aqueous solution, they all nevertheless retained a significant antimicrobial activity against Gram positive and Gram negative bacteria. These mimetics provide interesting starting points for an optimization program in the search for potent and novel antimicrobial compounds.

  转向形成的D-Pro-L-Pro模板常被用于促进环状蛋白表位模拟物中的规则β-发夹构象。这里研究了三种异构体的双芳基模板作为D-Pro-L-Pro的替代品，用于制备β-发夹肽模拟物。o,o'、o,m'和m,m'异构体的羧甲基和氨甲基取代的双芳基模板被引入到自然发生的阳离子抗菌肽protegrin I的新型宏环模拟物中。o-羧甲基-o'-氨甲基双芳基模板的存在使得宏环肽中出现了缓慢互变的厄尔托普异构体。尽管最终得到的模拟物在水溶液中未能形成稳定的β-发夹结构，它们仍保留了对革兰氏阳性和革兰氏阴性细菌的显著抗菌活性。这些模拟物为寻找强效和新型抗菌化合物的优化程序提供了有趣的出发点。