isothiocyanatoformic acid allyl ester | 55489-61-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: isothiocyanatoformic acid allyl ester
• 英文别名: Alloc-NCS；Alloc-isothiocyanate；allyloxycarbonyl isothiocyanate；N-Alloc-isothiocyanate；Carbonisothiocyanate, 2-propen-1-yl ester；prop-2-enyl N-(sulfanylidenemethylidene)carbamate
• CAS: 55489-61-7
• 化学式: C₅H₅NO₂S
• 分子量: 143.166
• InChiKey: IKWNDQWYEAOJDA-UHFFFAOYSA-N

物化性质

• 沸点：
  48.5-50.5 °C(Press: 7 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isothiocyanatoformic acid allyl ester 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 74.5h， 生成 N^α-(tert-butyloxycarbonyl)-N^ω-allyloxycarbonyl-N^ω′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yloxy)-L-arginine tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and Bioactivation of O-Glycosylated Prodrugs of the Natural Nitric Oxide Precursor N^ω-Hydroxy-l-arginine

  摘要：

  Naturally occurring N-omega-hydroxy-L-arginine (NOHA, 1) is the best substrate of NO synthases (NOS). The development of stable and bioavailable prodrugs would provide a pharmacologically valuable strategy for the treatment of cardiovascular diseases that are associated with endothelial dysfunction. To improve NOHAs druglike properties, we demonstrate that O-substitution by (glycosylic) acetal formation greatly increased the chemical stability of the hydroxyguanidine moiety and provided a nontoxic group that could be easily bioactivated by glycosidases. A straightforward synthetic concept was devised and afforded a series of diversely substituted prodrugs by O-conjugation of the hydroxyguanidine moiety with different monosaccharides. Systematic exploration of their bioactivation profile revealed that glucose-based prodrugs were more efficiently bioactivated than their galactose counterparts. NOS-dependent cytosolic NO release was quantified by automated fluorescence microscopy in a cell-based assay with murine macrophages. Glucose-based prodrugs performed particularly well and delivered cellular NO levels comparable to 1, demonstrating proof-of-concept.

  DOI：

  10.1021/acs.jmedchem.6b00810
• 作为产物：
  描述：

  potassium thioacyanate 、 氯甲酸烯丙酯 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 isothiocyanatoformic acid allyl ester
  参考文献：
  名称：

  含有吗啉代am单元的新型寡核苷酸类似物

  摘要：

  通过结合吗啉代核苷（为简化命名，我们将使用吗啉代核苷一词来指代其中核糖环被转化为吗啉的核苷类似物）与核苷间胍，将吗啉代am啶设计为寡核苷酸中的新阳离子单元。在此，开发了合成包含由吗啉代尿苷和5'-氨基-5'-脱氧胸苷形成的吗啉代am的寡核苷酸的方法。吗啉代am是通过Alloc-吗啉代碳硫代酰胺与5'-氨基核苷酸树脂的固相反应和Mukaiyama的试剂活化而产生的。两个14聚体合成了包含单个吗啉代am的寡核苷酸，并通过形成DNA双螺旋和三螺旋来研究它们的亲和特性。双工通过3'单元略微稳定，但如果位于内部，则不稳定。值得注意的是，三重链在pH 7.0下显着稳定。

  DOI：

  10.1016/j.tet.2008.11.069

文献信息

• The Use of Differential Receptors to Pattern Peptide Phosphorylation
  作者：Tianzhi Zhang、Nicola Y. Edwards、Marco Bonizzoni、Eric V. Anslyn

  DOI：10.1021/ja9041675

  日期：2009.8.26

  the receptors, three metal ions and three pH indicators are used to create a suite of 45 indicator displacement assays. The colorimetric data from the 45 sensing ensembles is collected in a 96-well plate reader, and linear discriminant analysis gives patterns resulting in 100% classification of the peptides. The approach demonstrates a generalizable principle to create pattern-based recognition protocols

  介绍了一种用于区分小肽及其磷酸化类似物的阵列传感方案。该技术涉及通过将随机肽附加到结合磷酸单酯的 C(3v) 对称支架创建的一系列受体。通过筛选技术选择了五个特定的肽序列。除了由受体中的肽产生的交叉反应外，还使用三种金属离子和三种 pH 指示剂来创建一套 45 种指示剂置换分析。来自 45 个传感集合的比色数据收集在 96 孔板读取器中，线性判别分析给出导致肽 100% 分类的模式。该方法展示了为复杂分析物创建基于模式的识别协议的通用原则。
• Synthesis of protected guanidinium linked dinucleoside incorporable into an oligonucleotide using solid phase DNA methodology
  作者：Dinesh A. Barawkar、Barry Linkletter、Thomas C. Bruice

  DOI：10.1016/s0960-894x(98)00251-0

  日期：1998.6

  The synthesis of novel fully protected guanidinium linked dinucleoside for incorporation into oligonucleotide using solid-phase DNA synthesis methodology was developed. The three different protecting groups selected allow different deprotection conditions.

  开发了使用固相DNA合成方法合成新的完全保护的胍连接的二核苷以掺入寡核苷酸中。选择的三个不同的保护基允许不同的脱保护条件。
• Studies of the Pyrimidine Derivatives. XXV. The Reaction of Alkoxycarbonylthiocyanates and Related Compounds with the Sodium Salt of Thiamine
  作者：Akira Takamizawa、Kentaro Hirai、Keiko Matsui

  DOI：10.1246/bcsj.36.1214

  日期：1963.9
• Combinatorial Solid-Phase Synthesis of Structurally Complex Thiazolylhydantoines
  作者：Josef Stadlwieser、Ernst P. Ellmerer-Müller、Andreas Takó、Najib Maslouh、Willi Bannwarth

  DOI：10.1002/(sici)1521-3773(19980605)37:10<1402::aid-anie1402>3.0.co;2-6

  日期：1998.6.5

  A nine-step (!) solid-phase synthesis and subsequent cleavage with cyclization from the polymeric support were the keys to preparing high-quality molecular libraries of thiazolylhydantoines 1 from modified amino acid building blocks. Each step in the synthesis is different. Because the final cyclization cleaves only molecules that have been successfully constructed, the products obtained are pure. R1 , R2 =alkyl; R3 =aryl, arylO; R4 =allyl.
• WO2021060980A5
  申请人：——

  公开号：WO2021060980A5

  公开（公告）日：2023-10-02