methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)salicylate | 119754-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)salicylate
• 英文别名: Methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)benzoate；methyl 2-hydroxy-5-(2-trimethylsilylethynyl)benzoate
• CAS: 119754-18-6
• 化学式: C₁₃H₁₆O₃Si
• 分子量: 248.354
• InChiKey: SVSDOLBGZNROSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.8±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)salicylate 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 三乙胺 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 4-{(E)-2-[3-(hydroxymethyl)phenyl]-1-ethenyl}-3-(hydroxymethyl)ethynylbenzene
  参考文献：
  名称：

  Preparation of Functionalised Aryl Alkynes as Precursors to Extended Cyclophanes

  摘要：

  The preparation of 2,6-substituted arylhalides and triflates is described. These compounds are suitable precursors for cyclophane formation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01002-9
• 作为产物：
  描述：

  5-碘水杨酸 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 硫酸 、 三乙胺 作用下， 反应 7.0h， 生成 methyl 2-hydroxy-5-((trimethylsilyl)ethynyl)salicylate
  参考文献：
  名称：

  Takalo, Harri; Kankare, Jouko; Haenninen, Elina, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 7, p. 448 - 454

  摘要：

  DOI：

文献信息

• Compounds containing an amino salicylic acid moiety linked to a
  申请人：Kabi Pharmacia AB

  公开号：US05302718A1

  公开（公告）日：1994-04-12

  A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomeric form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl. The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.

  公式为Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH)的化合物及其互变异构形式、盐、溶剂合物、C.sub.1-6烷基酯和药物组合物。Ph.sup.1和Ph.sup.2是苯环，但须满足羧基和羟基相对于彼此为邻位。Het包括一个可选择取代的杂环环，其中包括共轭双键并与NR中的氮结合。该化合物的特点在于A是一个稳定的桥梁，不易还原，因为它不是偶氮化合物，而且R是氢或较低的烷基。该发明还包括该化合物的制备以及其作为药物的用途，特别是用于治疗自身免疫性疾病。
• Metal Complex Lipids for Fluid–Fluid Phase Separation in Coassembled Phospholipid Membranes
  作者：Ryo Ohtani、Yuka Anegawa、Hikaru Watanabe、Yutaro Tajima、Masanao Kinoshita、Nobuaki Matsumori、Kenichi Kawano、Saeko Yanaka、Koichi Kato、Masaaki Nakamura、Masaaki Ohba、Shinya Hayami

  DOI：10.1002/anie.202102774

  日期：2021.6.7

  We demonstrate a fluid–fluid phase separation in 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) membranes using a metal complex lipid of type [Mn(L1)] (1; HL1=1-(2-hydroxybenzamide)-2-(2-hydroxy-3-formyl-5-hexadecyloxybenzylideneamino)ethane). Small amount of 1 produces two separated domains in DMPC, whose phase transition temperatures of lipids (Tc) are both lower than that of the pristine DMPC

  我们展示了使用 [Mn(L1)] 类型的金属复合脂质在 1,2-二肉豆蔻酰基-sn-甘油-3-磷酸胆碱 (DMPC) 膜中的流体-流体相分离( 1 ; HL1=1-(2-羟基苯甲酰胺) )-2-(2-羟基-3-甲酰基-5-十六烷氧基亚苄基氨基)乙烷)。的少量1中DMPC，其相转变温度的脂质（产生两个分离的域Ť Ç）均小于原始DMPC低。为DMPC的巨单层囊泡可变温度荧光显微镜/ 1杂种表明可见的相分离残留在流体相到37℃，这显然是在Ť ÇDMPC。这为金属复合脂质在流体膜中控制脂质分布的应用提供了新的维度。
• Substituted salicylic acids
  申请人：Pharmacia AB

  公开号：US05403930A1

  公开（公告）日：1995-04-04

  A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomic form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl. The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.

  该化合物的化学式为 Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH)，并包括其互变异构体、盐、溶剂合物、C.sub.1-6烷基酯和该化合物的药物组成物。其中，Ph.sup.1 和 Ph.sup.2 是苯环，但需满足羧基和羟基相对位于苯环的邻位。Het 包括一个可选取代的杂环，其中包括共轭双键并与 NR 中的氮原子结合。该化合物的特点是 A 是一种桥接基团，由于不是偶氮化合物，因此对还原稳定，而 R 为氢或低碳基。本发明还包括该化合物的制备方法以及其作为药物的用途，特别是用于治疗自身免疫性疾病。
• N-heterocyclic substituted salicylic acids
  申请人：Pharmacia AB

  公开号：US05556855A1

  公开（公告）日：1996-09-17

  A compound of the formula Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH) and tautomic form, salts, solvates, C.sub.1-6 alkyl esters and pharmaceutical compositions of the compound. Ph.sup.1 and Ph.sup.2 are benzene rings with the proviso that carboxy and hydroxy are ortho to one another. Het includes an optionally substituted heterocyclic ring which includes conjugated double bonds and binds to nitrogen in NR. The compound is characterized in that A is a bridge which is stable against reduction because it is not azo, and in that R is hydrogen or lower alkyl. The invention also includes the preparation of the compound and its use as a drug, particularly for treating autoimmune diseases.

  该化合物的化学式为Het--NR--SO.sub.2 --Ph.sup.2 --A--Ph.sup.1 (COOH)(OH)，其互变异构体、盐、溶剂化物、C.sub.1-6烷基酯和药物组合物。其中，Ph.sup.1和Ph.sup.2是苯环，但须满足羧基和羟基相对位于邻位。Het包括一个可选取代的杂环，其中包含共轭双键，并与NR中的氮原子结合。该化合物的特点在于，A是一个桥梁，因为它不是偶氮而稳定，R是氢或较低的烷基。本发明还包括该化合物的制备以及作为药物的用途，尤其用于治疗自身免疫性疾病。
• Selectivity Optimization of Substituted 1,2,3-Triazoles as α7 Nicotinic Acetylcholine Receptor Agonists
  作者：Kuntarat Arunrungvichian、Valery V. Fokin、Opa Vajragupta、Palmer Taylor

  DOI：10.1021/acschemneuro.5b00058

  日期：2015.8.19

  Three series of substituted anti-1,2,3-triazoles (IND, PPRD, and QND), synthesized by cycloaddition from azide and alkyne building blocks, were designed to enhance selectivity and potency profiles of a lead alpha 7 nicotinic acetylcholine receptor (alpha 7-nAChR) agonist, TTIn-1. Designed compounds were synthesized and screened for affinity by a radioligand binding assay. Their functional characterization as agonists and antagonists was performed by fluorescence resonance energy transfer assay using cell lines expressing transfected cDNAs, alpha 7-nAChRs, alpha 4 beta 2-nAChRs, and 5HT(3A), receptors, and a fluorescence cell reporter. In the END series, a tropane ring of TTIn-1, substituted at Ni, was replaced by mono- and bicyclic amines to vary length and conformational flexibility of a carbon linker between nitrogen atom and Ni of the triazole. Compounds with a two-carbon atom linker optimized binding with K-d's at the submicromolar level. Further modification at the hydrophobic indole of TTIn-1 was made in PPRD and QND series by fixing the amine center with the highest affinity building blocks in the IND series. Compounds from IND and PPRD series are selective as agonists for the alpha 7-nAChRs over alpha 4 beta 2-nAChRs and 5HT(3A) receptors. Lead compounds in the three series have EC50's between 28 and 260 nM. Based on the EC50, affinity, and selectivity determined from the binding and cellular responses, two of the leads have been advanced to behavioral studies described in the companion article (DOI: 10.1021/acschemneuro.5b00059).