H-MeArg(Tos)-OH | 74071-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: H-MeArg(Tos)-OH
• 英文别名: (N^α-Me)Arg(Tos)；H-(N-Me)Arg(Tos)-OH；MeArg(Tos)；(2S)-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-2-(methylamino)pentanoic acid
• CAS: 74071-60-6
• 化学式: C₁₄H₂₂N₄O₄S
• 分子量: 342.419
• InChiKey: JOZPJVUYVQQWCK-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  H-MeArg(Tos)-OH 在 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 2-甲基-2-丁醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 Boc(N^α-Me)Arg(Tos)-Gly-Asp(O-cHex)-Man(4-MeBzl)
  参考文献：
  名称：

  Ali; Bennett; Calvo, Journal of Medicinal Chemistry, 1994, vol. 37, # 6, p. 769 - 780

  摘要：

  DOI：
• 作为产物：
  描述：

  (Nα-Bzl)(Nα-Me)Arg(Tos) 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以37%的产率得到H-MeArg(Tos)-OH
  参考文献：
  名称：

  Development of a small RGD peptide fibrinogen receptor antagonist with potent antiaggregatory activity in vitro

  摘要：

  The development of potent antithrombotic agents from the fibrinogen platelet receptor binding sequences Fg-alpha 572-575-Arg-Gly-Asp-Ser- and Fg-gamma 400-411-HHLGGAKQAGDV, believed to be a cryptic RGD-type sequence, is described. The tetrapeptide Ac-RGDS-NH2 itself is capable of inhibiting platelet aggregation in vitro at high concentrations, IC50 91.3 +/- 0.1-mu-M [in vitro antiaggregatory activity employing dog platelet rich plasma (PRP)/ADP], due to low platelet fibrinogen receptor affinity, K(i) 2.9 +/- 1.9-mu-M (purified, reconstituted human platelet GPIIb/IIIa), relative to fibrinogen, K(i) 38.0 +/- 6.0 nM. The peptide is also unstable to plasma, suffering total loss of in vitro activity upon incubation in PRP for 3 h (T1/2 90 min). Only modest improvements in potency were achieved with linear analogues of Ac-RGDS-NH2, while dramatic results were achieved with cyclic analogues, culminating in the cyclic disulfide Ac-cyclo-S,S-[Cys-(N-alpha-Me)Arg-Gly-Asp-Pen]-NH2 (SK&F 106760) with improved plasma stability (100% activity after 3 h), affinity (K(i) 58 +/- 20 nM purified human receptor), and potency (IC50 0.36 +/- 0.4-mu-M dog PRP/ADP). The affinity of this peptide is 2 orders of magnitude greater than that of Ac-RGDS-NH2. The affinity of the analogue is also comparable to fibrinogen. This peptide constitutes a first potent small peptide entry into the class of novel antithrombotic agents called fibrinogen receptor antagonists.

  DOI：

  10.1021/jm00114a022

文献信息

• Des-proline-N-methylarginine vasopressins
  申请人：SmithKline Beckman Corporation

  公开号：US04687758A1

  公开（公告）日：1987-08-18

  Peptides having vasopressin antagonist activity are prepared by a peptide synthesizer to insert a N-methylarginine at the 7-position of the structure. An example of this series of compounds is [1-(.beta.-mercapto-.beta.,.beta.-cyclopentamethylenepropionic acid)-2-(O-ethyl-D-tyrosine)-4-valine-7-desproline-8-N-methylarginine-9-de sglycine]-vasopressin.

  具有抗利尿激素活性的肽类通过肽合成器制备，将N-甲基精氨酸插入结构的7位。这一系列化合物的一个例子是[1-(β-巯基-β,β-环戊亚甲基丙酸)-2-(O-乙基-D-酪氨酸)-4-缬氨酸-7-去脯氨酸-8-N-甲基精氨酸-9-去甘氨酸]-利尿激素。
• ALI, FADIA E.;HUFFMAN, WILLIAM F.;MARSHALL, GARLAND R.;MOORE, MICHAEL L.
  作者：ALI, FADIA E.、HUFFMAN, WILLIAM F.、MARSHALL, GARLAND R.、MOORE, MICHAEL L.

  DOI：——

  日期：——