2-(1,2,5-dithiazepan-5-yl)acetic acid | 148193-02-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1,2,5-dithiazepan-5-yl)acetic acid
• CAS: 148193-02-6
• 化学式: C₆H₁₁NO₂S₂
• 分子量: 193.291
• InChiKey: AVEQQQQOKKSAND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  91.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1,2,5-dithiazepan-5-yl)acetic acid 、 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 6-氯-1-羟基苯并三氮唑 作用下， 生成
  参考文献：
  名称：

  Chelate oxorhenium to assemble new integrin antagonists

  摘要：

  Assembly of independent chemical modules through oxorhenium coordination by a NS2 + S chelation motif was applied to the synthesis of RGD (Arg-Gly-Asp) analogs. Modules were assembled through oxorhenium chelation to give a series of 18 metal complexes in good yields and satisfactory purities. Screening of these oxorhenium coordinates as antagonists of integrins alpha V beta 3, alpha IIb beta 3 and alpha V beta 5 led to the identification of 3 bioactive compounds that exhibit submicromolar affinities for the 3 integrins. Preliminary studies showed that the corresponding oxotechnetium complexes are stable in mice plasma and therefore could be proposed for the molecular imaging of pathologies that overexpress integrins alpha V beta 3 and alpha V beta 5. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2011.03.008

文献信息

• Synthesis and biochemical evaluation of a cyclic RGD oxorhenium complex as new ligand of αVβ3 integrin
  作者：Marie Aufort、Marta Gonera、Nicolas Chaignon、Loïc Le Clainche、Christophe Dugave

  DOI：10.1016/j.ejmech.2009.02.022

  日期：2009.9

  We report the design of a new ligand of integrins that might be used for the molecular imaging of tumor neoangiogenesis. For this purpose, we designed a modified RGD tripeptide bearing a N-terminal N-bis(thioethyl)glycinate (NS2) motif and a thioethyl moiety at the C-terminus. Simultaneous coordination of an oxorhenium core by the NS2 and thioethyl moieties led to peptide cyclization and gave the corresponding monomers 13a and b (major isomer) resulting from the syn/anti-isomerism, along with dimers' species 16a and b. Cyclometallated peptide 13b showed the most promising activity with an IC50 of 86 nM for integrin alpha(V)beta(3) whereas it binds integrin a(IIb)beta(3) with an affinity lower by an order of magnitude. Labeling with [(99)mTc]oxotechnetium gluconate led exclusively to complex 17, the equivalent of compound 13b, which displayed satisfactory stabilities in mice plasma and towards glutathione. (C) 2009 Elsevier Masson SAS. All rights reserved.