4-(5-methyl-furan-2-yl)-benzoic acid methyl ester | 53355-26-3

• 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: 4-(5-methyl-furan-2-yl)-benzoic acid methyl ester
• 英文别名: methyl 4-(5-methylfuran-2-yl)benzoate
• CAS: 53355-26-3
• 化学式: C₁₃H₁₂O₃
• mdl: MFCD04039142
• 分子量: 216.236
• InChiKey: FJPNKLXXHWBEFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-methyl-furan-2-yl)-benzoic acid methyl ester 、 ((+/-)-4-benzoyl-2-methylpiperazin-1-yl)acetonitrile 在 lithium hexamethyldisilazane 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-(4-benzoyl-2-methylpiperazin-1-yl)-2-[4-(5-methylfuran-2-yl)phenyl]ethane-1,2-dione
  参考文献：
  名称：

  Heterobiaryl Human Immunodeficiency Virus Entry Inhibitors

  摘要：

  Previously disclosed HIV (human immunodeficiency virus) attachment inhibitors, exemplified by BMS 806 (formally BMS378806, 1), are characterized by a substituted indole or azaindole ring linked to a benzoylpiperazine via a ketoamide or sulfonamide group. In the present report, we describe the discovery of a novel series of potent HIV entry inhibitors in which the indole or azaindole ring of previous inhibitors is replaced by a heterobiaryl group. Several of these analogues exhibited IC(50) values of less than 5 nM in a pseudotyped antiviral assay, and compound 13k was demonstrated to exhibit potency and selectivity similar to those of I against a panel of clinical viral isolates. Moreover, current structure-activity relationship studies of these novel biaryl gp120 inhibitors revealed that around the biaryl, a fine crevice might exist in the gp120 binding site. Taken in sum, these data reveal a hitherto unsuspected flexibility in the structure-activity relationships for these inhibitors and suggest new avenues for exploration and gp120 inhibitor design.

  DOI：

  10.1021/jm900330x
• 作为产物：
  描述：

  1-(p-methoxycarbonylphenyl)pent-2-yne-1,4-diol 在 苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以72%的产率得到4-(5-methyl-furan-2-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  2,5-Disubstituted furans from 1,4-alkynediols

  摘要：

  1-4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)(3)(CO)H-2 with Xantphos at 1 mol % loading. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.05.069

文献信息

• Radical Arylation of Phenols, Phenyl Ethers, and Furans
  作者：Alexander Wetzel、Gerald Pratsch、Roman Kolb、Markus R. Heinrich

  DOI：10.1002/chem.200902927

  日期：2010.2.22

  efficient, and cost‐effective new access to diversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxy groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a β‐secretase inhibitor and the synthesis of a calcium‐channel modulator.

  对位取代苯酚和苯基醚的自由基芳基化反应在邻位具有良好的区域选择性相对于羟基或烷氧基的位置。反应是用芳基氮鎓盐作为芳基自由基源，氯化钛（III）作为还原剂，和稀盐酸作为溶剂进行的。取代的联芳基得自羟基和烷氧基取代的苄胺，苯乙胺和芳香族氨基酸。所描述的方法提供了快速，高效和经济高效的新途径，以获取功能多样的联苯醇和醚。游离酚羟基，芳族和脂族胺以及氨基酸亚结构均具有良好的耐受性。该方法适用性的两个例子是β分泌酶抑制剂的部分合成和钙通道调节剂的合成。
• Piperazine and piperidine biaryl derivatives
  申请人：Lu Jian Rong

  公开号：US20070259879A1

  公开（公告）日：2007-11-08

  This invention relates to piperazine and piperidine biaryl compounds of Formula (I): or a pharmaceutically acceptable prodrug, salt, polymorph, solvate, enantiomer, diastereomer, racemate, mixture of stereoisomers thereof, or derivative thereof; and to processes for preparing the compounds or pharmaceutical compositions containing the same. The compounds and pharmaceutical compositions of the present invention are provided for use in the treatment of HIV infection and/or AIDS.

  本发明涉及公式（I）的哌嗪和哌啶双芳基化合物： 或其药物可接受的前药、盐、多晶形、溶剂化物、对映体、非对映体、外消旋体、其立体异构体混合物或衍生物；以及用于制备化合物或含有相同化合物的制药组合物的过程。本发明的化合物和制剂用于治疗HIV感染和/或艾滋病。
• US7582658B2
  申请人：——

  公开号：US7582658B2

  公开（公告）日：2009-09-01
• [EN] PIPERAZINE AND PIPERIDINE BIARYL DERIVATIVES<br/>[FR] DERIVES DE PIPERAZINE ET PIPERIDINE BIARYLE
  申请人：TRIMERIS INC

  公开号：WO2007103456A2

  公开（公告）日：2007-09-13

  [EN] This invention relates to piperazine and piperidine biaryl compounds of Formula (I) or a pharmaceutically acceptable prodrug, salt, polymorph, solvate, enantiomer, diastereomer, racemate, mixture of stereoisomers thereof, or derivative thereof; and to processes for preparing the compounds or pharmaceutical compositions containing the same. The compounds and pharmaceutical compositions of the present invention are provided for use in the treatment of HIV infection and/or AIDS.
  [FR] L'invention concerne des composés pipérazine et pipéridine biaryle de formule (I) ou un promédicament, un sel, un polymorphe, un solvate, un énantiomère, un diastéréomère, un racémate, un mélange de stéréoisomères pharmaceutiquement acceptables de ceux-ci, ou leurs dérivés ; et des procédés destinés à la préparation des composés ou des compositions pharmaceutiques les contenant. Les composés et compositions pharmaceutiques de la présente invention concernent une utilisation dans le traitement de l'infection par le HIV et/ou du SIDA.
• Heterobiaryl Human Immunodeficiency Virus Entry Inhibitors
  作者：Rong-Jian Lu、John A. Tucker、Jason Pickens、You-An Ma、Tatiana Zinevitch、Olga Kirichenko、Vitalii Konoplev、Svetlana Kuznetsova、Sergey Sviridov、Enugurthi Brahmachary、Alisher Khasanov、Charles Mikel、Yang Yang、Changhui Liu、Jian Wang、Stephanie Freel、Shelly Fisher、Alana Sullivan、Jiying Zhou、Sherry Stanfield-Oakley、Brian Baker、Jeff Sailstad、Michael Greenberg、Dani Bolognesi、Brian Bray、Barney Koszalka、Peter Jeffs、Cynthia Jeffries、Alexander Chucholowski、Connie Sexton

  DOI：10.1021/jm900330x

  日期：2009.7.23

  Previously disclosed HIV (human immunodeficiency virus) attachment inhibitors, exemplified by BMS 806 (formally BMS378806, 1), are characterized by a substituted indole or azaindole ring linked to a benzoylpiperazine via a ketoamide or sulfonamide group. In the present report, we describe the discovery of a novel series of potent HIV entry inhibitors in which the indole or azaindole ring of previous inhibitors is replaced by a heterobiaryl group. Several of these analogues exhibited IC(50) values of less than 5 nM in a pseudotyped antiviral assay, and compound 13k was demonstrated to exhibit potency and selectivity similar to those of I against a panel of clinical viral isolates. Moreover, current structure-activity relationship studies of these novel biaryl gp120 inhibitors revealed that around the biaryl, a fine crevice might exist in the gp120 binding site. Taken in sum, these data reveal a hitherto unsuspected flexibility in the structure-activity relationships for these inhibitors and suggest new avenues for exploration and gp120 inhibitor design.