(4S)-1-Fmoc-4-(Allyloxycarbonylamino)-L-proline | 274676-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4S)-1-Fmoc-4-(Allyloxycarbonylamino)-L-proline
• 英文别名: (2S,4S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-(prop-2-enoxycarbonylamino)pyrrolidine-2-carboxylic acid
• CAS: 274676-10-7
• 化学式: C₂₄H₂₄N₂O₆
• 分子量: 436.464
• InChiKey: DSGCPQRUOSTFEF-BTYIYWSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-1-Fmoc-4-(Allyloxycarbonylamino)-L-proline 、 2,4-二氯苯酚呋喃 、 2,4-二氯苯甲醛 、 Fmoc-Pbf-L-精氨酸 以4%的产率得到cis-(L-arginyl)amino-N-(2,4-dichlorophenylmethyl)-L-proline 2,4-dichlorophenethylamide
  参考文献：
  名称：

  Design and Synthesis of Indole-Based Peptoids as Potent Noncompetitive Antagonists of Transient Receptor Potential Vanilloid 1

  摘要：

  The vanilloid receptor subunit 1, or transient receptor potential vanilloid I (TRPV1), integrates physical and chemical stimuli in the peripheral nervous system, playing a key role in inflammatory pain. Identification of potent TRPV1 antagonists is thus an important goal of current neuropharmacology. Herein, we describe the solid-phase synthesis of a series of indole-based peptoids (N-alkylglycines) and the biological activity of the peptoids as novel TRPV1 antagonists. The potency and selectivity of the compounds were determined by electrophysiological recordings in Xenopus oocytes. The most potent and selective noncompetitive TRPV1 antagonist of the series, compound 7, represents an interesting pharmacophoric structure for analgesic lead optimization.

  DOI：

  10.1021/jm070612v

文献信息

• Template-fixed peptidommetics as inhibitors of serine proteases
  申请人：Obrecht Daniel

  公开号：US20050187145A1

  公开（公告）日：2005-08-25

  Template-fixed β-hairpin peptidomimetics of the general formulae (1), wherein Z is a template-fixed chain of 7 to 11 α-amino acid residues which, depending on their positions in the chain (counted starting formteh N-terminal amino acid) are Gly, or Pro, or of certain types which, as the remaining symbols in the aove formulae, are defined in the description and the claims, and salts thereof, have the property to inhibit proteases, in particular serine proteases. These β-hairpin peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  通式（1）中，Z是一个由7到11个α-氨基酸残基组成的模板固定链，根据它们在链中的位置（从N-末端氨基酸开始计数），它们可以是甘氨酸，脯氨酸或某些类型，这些类型由上述式子中的其余符号在描述和权利要求中定义，并且其盐具有抑制蛋白酶，特别是丝氨酸蛋白酶的性质。这些β-发夹仿生肽可以通过基于混合固体和溶液相合成策略的过程制造。
• TEMPLATE-FIXED PEPTIDOMIMETICS WITH ANTIMICROBIAL ACTIVITY
  申请人：Polyphor Ltd.

  公开号：EP1363934B1

  公开（公告）日：2014-10-08
• TEMPLATE-FIXED PEPTIDOMIMETICS AS INHIBITORS OF SERINE PROTEASES
  申请人：Polyphor Ltd.

  公开号：EP1458747B1

  公开（公告）日：2009-02-11
• Template-fixed peptidomimetics with antimicrobial activity
  申请人：——

  公开号：US20040171066A1

  公开（公告）日：2004-09-02

  Template-fixed &bgr;-hairpin peptidomimetics of the general formulae (I) and (II) wherein Z, Z1 and Z2 are template-fixed chains of 8 to 16 &agr;-amino acid residues which, depending on their positions in the chain (counted starting from the N-terminal amino acid) are Gly, or Pro, or of certain types which, as the remaining symbols in the above formulae, are defined in the description and the claims, and salts thereof, have the property to inhibit the growth of or to kill microorganisms and cancer cells. They can be used as disinfectants for foodstuffs, cosmetics, medicaments or other nutrient-containing materials or as medicaments to treat or prevent infections or diseases related to such infections and/or cancer. These &bgr;-hairpin peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy. 1
• US7253146B2
  申请人：——

  公开号：US7253146B2

  公开（公告）日：2007-08-07