1-甲磺酰氧基-3-(4-甲氧基苯基)丙烷 | 72456-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-甲磺酰氧基-3-(4-甲氧基苯基)丙烷
• 英文名称: 3-(4-methoxyphenyl)propyl methanesulfonate
• 英文别名: 1-methanesulfonyloxy-3-(4-methoxyphenyl)propane
• CAS: 72456-64-5
• 化学式: C₁₁H₁₆O₄S
• 分子量: 244.312
• InChiKey: BUFWKVCDMXCQFK-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  411.4±28.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-甲磺酰氧基-3-(4-甲氧基苯基)丙烷 在 sodium azide 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-甲氧基苯基)-丙胺
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers:  Drugs for Cystic Fibrosis and Chronic Bronchitis

  摘要：

  Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent shortcircuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

  DOI：

  10.1021/jm051134w
• 作为产物：
  描述：

  3-(4-甲氧基苯基)丙酸 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-甲磺酰氧基-3-(4-甲氧基苯基)丙烷
  参考文献：
  名称：

  新型苯并吡啶并二氮杂卓类化合物可能作为潜在的抗肿瘤活性药物。

  摘要：

  报道了可以被视为E-7010的限制性类似物的新型噻二氮杂卓衍生物的合成。评价这些分子对鼠L1210白血病细胞系的抗增殖活性。对具有最高细胞毒性化合物的L1210细胞进行的流式细胞术研究表明，细胞周期G2 / M期的细胞蓄积，其中四倍体细胞的百分比很高（8N DNA含量）。用化合物2b，4b，4e，4g和4i观察到亚微摩尔的细胞毒性。发现其中两种化合物2b和4b是微管蛋白聚合的有效抑制剂，而去氧鬼臼毒素的IC50分别为3.8和2.4 microM。发现苯并吡啶并噻二氮杂卓的吡啶基氮上的4-甲氧基苯基乙基取代对于抗增殖活性是必不可少的。化合物2b和4b的体外活性使苯并吡啶并噻二氮杂二氧化物成为一种有前景的新型微管蛋白粘合剂，需要进一步的体内评估。

  DOI：

  10.1021/jm0503897

文献信息

• Calcitonin gene related peptide receptor antagonists
  申请人：——

  公开号：US20040204397A1

  公开（公告）日：2004-10-14

  The present invention relates to compounds of Formula (I) 1 as antagonists of calcitonin gene-related peptide receptors (“CGRP-receptor”), pharmaceutical compositions comprising them, methods for identifying them, methods of treatment using them and their use in therapy for treatment of neurogenic vasodilation, neurogenic inflammation, migraine and other headaches, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.

  本发明涉及式（I）的化合物作为降钙素基因相关肽受体（“CGRP受体”）拮抗剂，包括它们的药物组合物，用于识别它们的方法，使用它们进行治疗的方法，以及它们在治疗神经源性血管舒张、神经源性炎症、偏头痛和其他头痛、热损伤、循环休克、与绝经相关的潮红、气道炎症性疾病（如哮喘和慢性阻塞性肺病（COPD））以及其他可以通过拮抗CGRP受体来治疗的疾病的治疗中的用途。
• Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents
  作者：Claire Andersen、Vincent Ferey、Marc Daumas、Patrick Bernardelli、Amandine Guérinot、Janine Cossy

  DOI：10.1021/acs.orglett.0c02115

  日期：2020.8.7

  The development of a copper-catalyzed cross-coupling between primary and secondary (pseudo)halides and bicyclopentyl Grignard reagents is reported. Highly strained bicyclopentanes can be cross-coupled with a large panel of primary alkyl mesylates and secondary alkyl iodides. The catalytic system is simple and cheap, and the reaction is general and chemoselective.

  据报道，伯和仲（伪）卤化物与双环戊基格氏试剂之间存在铜催化的交叉偶联。高度应变的双环戊烷可与一大批伯烷基甲磺酸酯和仲烷基碘化物交联。该催化体系简单且便宜，并且反应是一般的和化学选择性的。
• Saturated heterocyclic carboxamide derivatives
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US04987132A1

  公开（公告）日：1991-01-22

  A saturated heterocyclic carboxamide derivative of the following general formula (I) and salts thereof which have platelet activating factor (PAF) antagonizing activity. ##STR1##

  以下是通用公式（I）的饱和杂环羧酰胺衍生物及其盐，具有血小板活化因子（PAF）拮抗活性。
• The synthesis of three isotopomers of 2-methyl-2-(4-[3-[1-(4-methylbenzyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]propyl]phenoxy)propionic acid, a potent and selective peroxisome proliferator-activated receptor alpha agonist
  作者：Fengjiun Kuo、Dean K. Clodfelter、Nagy A. Farid、William J. Wheeler、Lennon H. McKendry

  DOI：10.1002/jlcr.1395

  日期：2007.7

  Although fenofibrate (1a) is commercially available and clinically effective in lowering serum triglycerides, its activity and sub-type selectivity at the PPARα receptors are only moderate; therefore, there exists a need for more potent and sub-type selective PPARα agonists. To that end, discovery efforts have identified 2-methyl-2-(4-[3-[1-(4-methylbenzyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]propyl]phenoxy)propionic acid (2), a potent and selective human PPARα receptor agonist. In support of pre-clinical ADME studies and bioanalysis, three isotopomers of 2 have been synthesized. The results of these efforts are described below. Copyright © 2007 John Wiley & Sons, Ltd.

  非诺贝特（1a）虽已上市并能有效地降低血清甘油三酯，其在过氧化物酶体增殖激活受体α（PPARα）上的活性和亚型选择性仅属中等水平；因此，需要更强效且更具亚型选择性的PPARα激动剂。为此，研发过程中发现了2-甲基-2-(4-[3-[1-(4-甲基苄基)-5-氧代-4,5-二氢-1H-[1,2,4]三唑-3-基]丙基]苯氧基)丙酸（化合物2），它是一种强效且选择性的人源PPARα受体激动剂。为了支持临床前ADME研究和生物分析，合成了化合物2的三种同位素标记物。以下将详细描述这些成果。版权所有 © 2007 John Wiley & Sons, Ltd.
• 7-oxabicycloheptyl substituted heterocyclic amide or ester prostaglandin
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05100889A1

  公开（公告）日：1992-03-31

  7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasopastic disease have the structural formula ##STR1## wherein m is 1, 2 or 3; n is 1, 2, 3 or 4; Z is --(CH.sub.2).sub.2 --, --CH.dbd.CH-- or ##STR2## wherein Y is O, a single bond or vinyl, with the proviso that when n is 0, if Z is ##STR3## then Y cannot be O, and Z is --CH.dbd.CH--, n is 1, 2, 3 or 4; and when Y=vinyl, n=0; R is CO.sub.2 H, CO.sub.2 lower alkyl, CH.sub.2 OH, CO.sub.2 alkali metal, CONHSOR.sup.3, CONHR.sup.3a or --CH.sub.2 --5-tetrazolyl, X is O, S or NH; and where R.sup.1, R.sup.2, R.sup.3 and R.sup.3a are as defined herein.

  7-氧杂双环庚烷取代前列腺素类似物在治疗血栓性和血管痉挛性疾病中有用，其结构式为##STR1##其中m为1、2或3；n为1、2、3或4；Z为--(CH.sub.2).sub.2 --、--CH.dbd.CH--或##STR2##其中Y为O、单键或乙烯基，但当n为0时，若Z为##STR3##则Y不能为O，Z为--CH.dbd.CH--，n为1、2、3或4；当Y=乙烯基时，n=0；R为CO.sub.2 H、CO.sub.2 较低烷基、CH.sub.2 OH、CO.sub.2 碱金属、CONHSOR.sup.3、CONHR.sup.3a或--CH.sub.2 --5-四唑基，X为O、S或NH；R.sup.1、R.sup.2、R.sup.3和R.sup.3a的定义如本文所述。