2-[(9H-fluoren-9-ylmethoxycarbonylamino)-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetic acid | 808733-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[(9H-fluoren-9-ylmethoxycarbonylamino)-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetic acid
• CAS: 808733-37-1
• 化学式: C₂₃H₂₆N₂O₆
• 分子量: 426.469
• InChiKey: AGCJDMSBEMIIJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(9H-fluoren-9-ylmethoxycarbonylamino)-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetic acid 、 Fmoc-甘氨酸 、 FMOC-L-精氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2S)-2-[[2-[[[2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-(carboxymethyl)amino]acetyl]amino]-3-methylbutanoic acid
  参考文献：
  名称：

  Design, synthesis and cardioprotective effect of a new class of dual-acting agents: Phenolic tetrahydro-β-carboline RGD peptidomimetic conjugates

  摘要：

  In this study, a new class of phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates was designed and synthesized. The radical scavenging activities of these newly synthesized compounds 12a-c were evaluated in PC 12 cell survival assays. The NO scavenging activities of these compounds were confirmed in the acetylcholine-induced vasorelaxation assay. Compounds 12a-c were efficacious in a rat arterial thrombosis model, and were active in ADP- or PAF-induced in vitro platelet aggregation assays, which Suggests these compounds also possess anti-thrombotic activity. The beneficial effects of dual-acting agent 12c were demonstrated on the ischemia-reperfusion induced cardiac infarct size and oxidative change in an in vivo rat model. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.022
• 作为产物：
  描述：

  Methyl 2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-(phenylmethoxycarbonylamino)amino]acetate 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 calcium chloride 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 37.5h， 生成 2-[(9H-fluoren-9-ylmethoxycarbonylamino)-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetic acid
  参考文献：
  名称：

  一种Fmoc-Aza-β³Asp(OtBu)-OH的合成方法

  摘要：

  本发明公开了一种Fmoc‑Azaβ 3 Asp(OtBu)‑OH的合成方法：将水合肼和氯甲酸苄酯发生亲核取代得到肼基甲酸苄酯，然后在N，N‑二异丙基乙胺存在下，所述的肼基甲酸苄酯与溴乙酸叔丁酯的发生亲核取代反应，得到式C1所示的化合物1和式C2所示的化合物2；将所得式C1所示的化合物1与溴乙酸甲酯发生亲核取代得到式C3所示的化合物3；将所得式C3所示的化合物3在催化剂Pd/C作用下，在H 2 气氛下反应得到式C4所示的化合物4；将所得式C4所示的化合物4与FmocOSu混合，在NaHCO 3 作用下，得到式C5所示的化合物5；将MeOH与式C5所示的化合物5发生水解反应，得到式C6所示的目标产物Fmoc‑Azaβ 3 Asp(OtBu)‑OH。本发明所述的制备方法，反应条件温和，操作简便，路线简单高效。

  公开号：

  CN108129356A

文献信息

• Peptide analogues comprising at least one type of aminoacylaza-$g(b)<sp>3</sp>and the use thereof, in particular for therapy
  申请人：Baudy Floc'h Michele

  公开号：US20110044974A1

  公开（公告）日：2011-02-24

  The object of the present invention is analogues of peptides or parent proteins, these peptide analogues, comprising at least one aza-β 3 aminoacyl residue, and also their uses in pharmaceutical compositions or for the diagnosis of pathologies wherein the aforesaid peptides or parent proteins are involved.

  本发明的对象是肽或母体蛋白的类似物，这些肽类似物包括至少一个aza-β3氨基酰残基，并且它们在药物组合物中的用途或用于诊断涉及上述肽或母体蛋白的病理的用途。
• Preparation of new monomers aza-β3-aminoacids for solid-phase syntheses of aza-β3-peptides
  作者：Olivier Busnel、Michèle Baudy-Floc’h

  DOI：10.1016/j.tetlet.2007.06.082

  日期：2007.8

  The preparation of new NO-Fmoc-protected aza-beta(3)-amino acids (aza-beta(3)-aa) with proteinogenic side chains as well as their N-beta-Fmoc, N-beta-Cbz or N-beta-Boc aza-beta(3)-amino esters (from Pro, Asn, Asp, Glu, Gln) by successive nucleophilic substitutions will be described. (c) 2007 Elsevier Ltd. All rights reserved.
• US9017673B2
  申请人：——

  公开号：US9017673B2

  公开（公告）日：2015-04-28
• [EN] PEPTIDE ANALOGUES COMPRISING AT LEAST ONE TYPE OF AMINOACYL AZA- DOLLAR G(B)<3> AND THE USE THEREOF, IN PARTICULAR FOR THERAPY<br/>[FR] ANALOGUES PEPTIDIQUES COMPRENANT AU MOINS UN RESIDU AZA-ß<3> AMINOACYLE, ET LEURS UTILISATIONS, NOTAMMENT EN THERAPIE
  申请人：CT NAT DE LA RECH SCIENTIQUE

  公开号：WO2004111086A2

  公开（公告）日：2004-12-23

  La présente invention a pour objet des analogues de peptides ou protéines parents, ces analogues peptidiques, comprenant au moins un résidu aza-ß3 aminoacyle, ainsi que leurs utilisations dans des compositions pharmaceutiques ou pour le diagnostic de pathologies dans lesquelles sont impliqués les peptides ou protéines parents susmentionnés.
• Design, synthesis and cardioprotective effect of a new class of dual-acting agents: Phenolic tetrahydro-β-carboline RGD peptidomimetic conjugates
  作者：Wei Bi、Jianhui Cai、Sanguang Liu、Michèle Baudy-Floc’h、Lanrong Bi

  DOI：10.1016/j.bmc.2007.08.022

  日期：2007.11

  In this study, a new class of phenolic tetrahydro-beta-carboline RGD peptidomimetic conjugates was designed and synthesized. The radical scavenging activities of these newly synthesized compounds 12a-c were evaluated in PC 12 cell survival assays. The NO scavenging activities of these compounds were confirmed in the acetylcholine-induced vasorelaxation assay. Compounds 12a-c were efficacious in a rat arterial thrombosis model, and were active in ADP- or PAF-induced in vitro platelet aggregation assays, which Suggests these compounds also possess anti-thrombotic activity. The beneficial effects of dual-acting agent 12c were demonstrated on the ischemia-reperfusion induced cardiac infarct size and oxidative change in an in vivo rat model. (C) 2007 Elsevier Ltd. All rights reserved.