symmetric anhydride of Boc-Tyr(Bzl)-OH | 37662-17-2

• 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: symmetric anhydride of Boc-Tyr(Bzl)-OH
• CAS: 37662-17-2
• 化学式: C₄₂H₄₈N₂O₉
• 分子量: 724.851
• InChiKey: OKCMGZIQPUSBOL-ZPGRZCPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  138.49
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  symmetric anhydride of Boc-Tyr(Bzl)-OH 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 23.0~25.0 ℃ 、330.95 kPa 条件下， 反应 24.5h， 生成 1,1-dimethylethyl <1-<(4-hydroxyphenyl)methyl>-2-oxo-2-<2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)3-oxo-9-<(5,6,7,13-tetrahydro-5,13-dioxoquinazolino<3,2-a><1,4>benzodiazepin-7-yl)methyl>-1H-imidazo-<1,2-a>indol010yl>ethyl>carbonic acid ester
  参考文献：
  名称：

  Cholecystokinin antagonists. Synthesis of asperlicin analogs with improved potency and water solubility

  摘要：

  Seventeen analogues of the selective, competitive cholecystokinin (CCK) antagonist asperlicin 1 were prepared. These compounds were tested as inhibitors of the binding of [125I]CCK to rat pancreas and guinea pig brain receptors. Compounds 4, 7, and 8 were more potent than asperlicin on the pancreatic CCK receptor. One analogue, 17, displayed potency equivalent to asperlicin on the pancreas CCK receptor and showed a marked improvement in aqueous solubility, thereby facilitating the use of this class of CCK antagonists in physiological and pharmacological studies.

  DOI：

  10.1021/jm00160a024
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 symmetric anhydride of Boc-Tyr(Bzl)-OH
  参考文献：
  名称：

  A Simple Preparation of Symmetrical Anhydrides ofN-Alkyloxycarbonylamino Acids

  摘要：

  DOI：

  10.1055/s-1978-24944

文献信息

• Polymer-supported synthesis of protected peptide segments on a photosensitive o-nitro(a-methyl)bromobenzyl resin
  作者：A. Ajayaghosh、V.N. Rajasekharan Pillai

  DOI：10.1016/s0040-4020(01)90104-8

  日期：1988.1

  The preparation of a new polystyrene support containing the photodetachable -nitro(α -methyl)benzyl anchoring group and its application in the solid phase synthesis of fully protected C-terminal peptides are described, The preparation of the photosensitive resin involves a 4-step polymer-analogous reaction starting from 1 %-divinyl benzene crosslinked polystyrene. Amino acid units were incorporated

  描述了一种新型的含有光可分离的-硝基（α-甲基）苄基锚定基团的聚苯乙烯载体的制备及其在完全保护的C-末端肽的固相合成中的应用。光敏树脂的制备涉及4步聚合物-类似反应从1％-二乙烯基苯交联的聚苯乙烯开始。按照标准固相肽合成方法，将氨基酸单元掺入该树脂中，并在中性条件下于350 nm通过光解从载体上裂解肽，总收率为40％至50％。肽通过就位的仲酯键连接至硝基是允许肽从支持物光解裂解的因素。
• Synthesis of chemoreversible prodrugs of ara-C with variable time-release profiles. Biological evaluation of their apoptotic activity
  作者：Peter Wipf、Wenjie Li、Christianah M. Adeyeye、James M. Rusnak、John S. Lazo

  DOI：10.1016/0968-0896(96)00153-8

  日期：1996.10

  N-4-Dipeptidyl slow-release forms of the anticancer drug ara-C were prepared by acylation of the lithiated nucleotide with 4,4-dialkyloxazolinones. An azapeptide prodrug of am-C was obtained by condensation of an amino acid hydrazide with an activated nucleotide urea. The use of unnatural amino acid residues at N-4 prevented nonspecific proteolytic cleavage in biological medium. Aln-C prodrugs 10, 15, 17, and 19 released active drug with half-lives from a few minutes to several days, respectively. Activation via intramolecular N-4-deacylation did not require enzymatic intervention but was strictly dependent on the structure of the peptide chain. The prodrugs 10, 15, and 17 produced similar growth inhibition as ara-C in cultured murine leukemia cells while the azapeptide prodrug 19 was less potent reflecting the slow release of active drug with this compound. All four prodrugs retained the ability to induce apoptosis in human HL-60 leukemia cells with kinetics dictated by the rate of intramolecular N-4-deacylation. This the first demonstration for the control of apoptotic cell death by the modulation of drug release from prodrugs. Copyright (C) 1996 Elsevier Science Ltd