methyl 2-(1-tosyl-3-pyrrolyl)acetate | 138779-98-3

• 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-(1-tosyl-3-pyrrolyl)acetate
• 英文别名: N-tosyl-(1H-pyrrol-3-yl)acetic acid methyl ester；methyl 2-(1-tosylpyrrol-3-yl)acetate；methyl 2-[3-(1-N-tosylpyrrole)]acetate；methyl 1-tosylpyrrole-3-acetate；Methyl 2-[1-(4-methylphenyl)sulfonylpyrrol-3-yl]acetate
• CAS: 138779-98-3
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: RPTHIFDXAAOPDG-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±47.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-tosyl-3-pyrrolyl)acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以80%的产率得到(吡咯-3-基)-乙酸
  参考文献：
  名称：

  Synthesis and Polymerization of 2-(3-Pyrrolyl)acetic Acid Derivatives from Pyrrole

  摘要：

  The synthesis of the 3-pyrrylacetic acid as well as the study of its esterification conditions are described. The new materials thus obtained are electropolymerized.

  DOI：

  10.1080/00397919608003488
• 作为产物：
  描述：

  1-(对甲苯磺酰基)吡咯 在 aluminum (III) chloride 、 thallium(III) nitrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.92h， 生成 methyl 2-(1-tosyl-3-pyrrolyl)acetate
  参考文献：
  名称：

  Synthesis of novel pyrrolyl-indomethacin derivatives

  摘要：

  In the present work, we report the synthesis of the novel esters of indomethacin (IDMC) and an ester of reduced IDMC. For this purpose, 1DMC is covalently bound by using a spacer chain to the pyrrole (Py) in the 3-position. The innovative pyrrole-indomethacin (3-Py-IDMC) derivates show no cytotoxic effects in primary calvarial osteoblasts. The designed IDMC derivates have been studied because they could be injected locally as a component of polymeric micro-particles. In fact, the new 3-Py-IDMC derivatives will assure their further polymerization since the 2- and 5-monomer positions are free. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.008

文献信息

• Pyrroles substituted by oligonucleotides
  申请人：Mandrand Bernard

  公开号：US20060189555A1

  公开（公告）日：2006-08-24

  The invention relates to novel pyrrole derivatives of the formula (I) which make it possible to immobilize and address oligonucleotides by electropolymerization. Said invention also relates to thus produced electroactive polymers and to methods for using them for detecting, identifying and dosing analytes in a sampe. (I) wherein R 1 is one type of oligonucleotide, Y is S or O, X is a spacer arm selected from —(CH 2 )—O—, —(CH 2 )PO—[(CH 2 ) 2 —O] q —, —(CH2 )r ; —CO—NR—(CH 2)r -0-, —CH 2r —NCH 3 —(CH 2 ) r —O—, —CH 2 ) r CO—NR′—[CH 2 ) 2 —O] s —, —(CH 2 ) r NCH 3 [(CH 2 ) 2 —O]S—, R′ is H or CH 3 , n is an integer number ranging from 1 to 5, p is an integer number ranging from 1 to 2, q is an integer number ranging from 1 to 4, r is an integer number ranging from 1 to 3, r′ is an integer number ranging from 1 to 3, s is an integer number ranging from 1 to 3, n, p, q, r, r′ and s are identical or different, a pyrrole cycle is substituted in a position 2, 3, 4 or 5.

  该发明涉及公式（I）的新型吡咯衍生物，可以通过电聚合固定和寻址寡核苷酸。该发明还涉及因此产生的电活性聚合物，以及使用它们用于检测、鉴定和定量样品中的分析物的方法。在公式（I）中，R1是一种类型的寡核苷酸，Y是S或O，X是从—（CH2）—O—、—（CH2）PO—（（CH2）2—O）q—、—（CH2）r；—CO—NR—（CH2r）-O-、—CH2r—NCH3—（CH2）r—O—、—CH2rCO—NR′—（CH2）2—O）s—、—（CH2）rNCH3（（CH2）2—O）S—中选择的间隔臂，R′是H或CH3，n是从1到5的整数，p是从1到2的整数，q是从1到4的整数，r是从1到3的整数，r′是从1到3的整数，s是从1到3的整数，n、p、q、r、r′和s是相同或不同的，吡咯环在位置2、3、4或5上被取代。
• Synthesis and pharmacokinetic properties of novel cPLA2α inhibitors with 1-(carboxyalkylpyrrolyl)-3-aryloxypropan-2-one structure
  作者：Angelina Subeska、Jan Althaus、Theresa Hake、Walburga Hanekamp、Dominik Bettenworth、Dennis Mulac、Klaus Langer、Matthias Lehr

  DOI：10.1016/j.bmc.2022.117110

  日期：2023.1

  concentrations could be achieved after peroral administration of this type of compound. Since insufficient metabolic stability was suspected as the cause, structural modifications were made to optimize this property. These included the conversion of the aromatic into an aliphatic carboxylic acid function as well as the rigidification of the lipophilic structural elements. A selected pyrrole-3-propionic acid was

  1 位带有 3-芳氧基-2-氧代丙基残基的吲哚-5-羧酸已被证明是细胞溶质磷脂酶 A 2 α (cPLA 2 α) 的有效抑制剂，后者是一种参与促炎脂质介质形成的酶。不幸的是，在动物实验中，口服此类化合物后只能达到非常低的血浆浓度。由于怀疑代谢稳定性不足是原因，因此进行了结构修改以优化此特性。这些包括将芳香族转化为脂肪族羧酸功能以及亲脂性结构元素的刚性化。对选定的吡咯-3-丙酸进行了体内经口试验小鼠的生物利用度。然而，该化合物也不能达到更高的血浆浓度。使用 Caco2 细胞渗透测定法，发现所研究的物质是胃肠道外排转运蛋白的非常好的底物，这解释了它们经口吸收不佳的原因。
• Superhydrophobic Surfaces of Electrodeposited Polypyrroles Bearing Fluorinated Liquid Crystalline Segments
  作者：Thierry Darmanin、Elisabeth Taffin de Givenchy、Frederic Guittard

  DOI：10.1021/ma101914j

  日期：2010.11.23

  Two intrinsic properties of fluorinated tails (F butyl to F-octyl) were combined in the elaboration of superhydrophobic surfaces by electrochemical polymerization their promesogenic characteristic and their ability to increase both hydrophobicity and oleophobicity We report the synthesis and the characterization of pyrrole monomers bearing fluorinated liquid crystalline segments The electrodeposited corresponding polymer films were characterized by cyclic voltammetry, static and dynamic contact angle measurements, and scanning electron microscopy Sticky superhydrophobic surfaces were obtained with a F-hexyl or a F octyl tail The presence of mesogenic segments improves the surface hydrophobicity and increases the surface roughness, clearly observed with F butyl and F hexyl chains
• Structure−Activity Relationships of 2,<i>N</i>⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor
  作者：Hayamitsu Adachi、Krishnan K. Palaniappan、Andrei A. Ivanov、Nathaniel Bergman、Zhan-Guo Gao、Kenneth A. Jacobson

  DOI：10.1021/jm061278q

  日期：2007.4.1

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.
• [EN] A2 ADENOSINE RECEPTOR AGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS D'ADÉNOSINE A2
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009006089A3

  公开（公告）日：2009-04-09