3-苄氧基吡啶-2-羧酸苄基酯 | 170689-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苄氧基吡啶-2-羧酸苄基酯
• 英文名称: 3-benzyloxypyridine-2-carboxylic acid benzyl ester
• 英文别名: Benzyl 3-(benzyloxy)picolinate；benzyl 3-phenylmethoxypyridine-2-carboxylate
• CAS: 170689-52-8
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: WVVSMQGGICZYSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-苄氧基吡啶-2-羧酸苄基酯 在 氢氧化钾 、 草酰氯 、 TEA 作用下， 以 二氯甲烷 为溶剂， 生成 3-Benzyloxy-pyridine-2-carboxylic acid thiazol-2-ylamide
  参考文献：
  名称：

  Inhibitors of type I MetAPs containing pyridine-2-carboxylic acid thiazol-2-ylamide. Part 1: SAR studies on the determination of the key scaffold

  摘要：

  Systematic SAR studies on the HTS hit pyridine-2-carboxylic acid thiazol-2-ylamide (PACT) analogues revealed that the scaffold of OCAT is indispensable for the inhibition of type I MetAP. For effective inhibition of the enzyme, the most suitable position to modify is the 3-position of the pyridine ring of PCAT, and the best substituents are those containing O or N atoms connected directly with the pyridine ring. These findings provide useful information for the design and discovery of more potent inhibitors of type I MetAPs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.034
• 作为产物：
  描述：

  3-羟基-2-吡啶甲酸 、 溴甲苯 在 silver(l) oxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 以70%的产率得到3-苄氧基吡啶-2-羧酸苄基酯
  参考文献：
  名称：

  In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of N-(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes

  摘要：

  The first synthesis and biological evaluation of antibiotic 31 (A-33853) and its analogues are reported. Initial screening for inhibition of L. donovani, T. b. rhodesiense, T cruzi, and P. falciparum cultures followed by determination of IC50 in L. donovani and cytotoxicity on L6 cells revealed 31 to be 3-fold more active than miltefosine, a known antileishmanial drug, Compounds 14, 15, and 25 selectively inhibited L. donovani at nanomolar concentrations and showed much lower cytotoxicity.

  DOI：

  10.1021/jm801241n

文献信息

• Synthesis of key sandramycin analogs: systematic examination of the intercalation chromophore
  作者：Dale L. Boger、Jyun-Hung Chen、Kurt W. Saionz、Qing Jin

  DOI：10.1016/s0968-0896(97)10014-1

  日期：1998.1

  The preparation and examination of 2-22 constituting a systematic study of the chromophore of sandramycin (1) are detailed. Fluorescence quenching studies were used to establish binding constants for 1-24 within calf thymus DNA, within a single high affinity bis-intercalation binding site 5'-d(GCATGC)(2), and to establish the preference for sandramycin binding to 5'-d(GCXXGC)(2) where XX = AT, TA, GC, and CG. From the latter studies, sandramycin was found to exhibit a preference that follows the order: 5'-d(GCATGC)(2) > 5'-d(GCGCGC)(2), Delta Delta G degrees = 0.3 kcal/mol > 5'-d(GCTAGC)(2), 5'-d(GCCGGC)(2), Delta Delta G degrees = 0.6 kcal/mol although it binds with high affinity to all four deoxyoligonucleotides. The two highest affinity sequences constitute repeating 5'-PuPy motifs with each intercalation event occurring at a 5'-PyPu step. The most effective sequence constitutes the less stable duplex, contains the sterically most accessible minor groove central to the bis-intercalation site, and the ability to accept two gly-NH/T C2 carbonyl H-bonds identified in prior NMR studies. Similarly, the contribution of the individual structural features of the chromophore were assessed with the high affinity duplex sequence 5'-d(GCATGC)(2). To a first approximation, the cytotoxic properties were found to parallel trends established in the DNA binding affinities. The exception to this generalization was 4 which lacks the sandramycin chromophore phenol. Although typically 4-10x less potent than sandramycin against leukemia cell lines, it proved to be 1-10,000x more potent against melanomas, carcinomas, and adenocarcinomas exhibiting IC50 values of IpM-10 nM placing it among the most potent agents identified to date. Additionally, the first disclosure of the HIV-1 reverse transcriptase inhibitory activity of sandramycin (1) as well as that of its key analogs are described and define the chromophore structural features required for their exceptional potency. Two analogs, 18 and 3, roughly maintain the HIV-I reverse transcriptase inhibitory potency of 1 but exhibit substantially diminished cytotoxic activity (10(2) - 10(3)x). (C) 1998 Elsevier Science Ltd. All rights reserved.
• [EN] CALCILYTIC COMPOUNDS<br/>[FR] COMPOSÉ CALCILYTIQUE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010039913A1

  公开（公告）日：2010-04-08

  Novel calcilytic compounds, pharmaceutical compositions, methods of synthesis and methods of using them are provided.