N-benzyl-5-(1-(triphenylmethyl)imidazol-4-yl)-1-pentanesulfonamide | 220378-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-benzyl-5-(1-(triphenylmethyl)imidazol-4-yl)-1-pentanesulfonamide
• 英文别名: N-benzyl-5-(1-tritylimidazol-4-yl)pentane-1-sulfonamide
• CAS: 220378-78-9
• 化学式: C₃₄H₃₅N₃O₂S
• 分子量: 549.737
• InChiKey: NUNSJHOZTOCJKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-5-(1-(triphenylmethyl)imidazol-4-yl)-1-pentanesulfonamide 在 三氟乙酸 作用下， 生成 5-(1H-imidazol-4-yl)pentane-1-sulfonic acid benzylamide
  参考文献：
  名称：

  ω-(Imidazol-4-yl)alkane-1-sulfonamides: a new series of potent histamine H3 receptor antagonists

  摘要：

  omega-(1H-imidazol-4-yl)alkane-1-sulfonamides were prepared and found to be potent histamine H-3 receptor antagonists. High receptor affinity and a low difference in the data between the bioassays were achieved with 5-(1H-imidazol-4-yl)pentane-1-sulfonic acid 4-chlorobenzylamide (16). Good in vitro profiles were also obtained for 2-hydroxysulfonamide and vinylsulfonamide analogues. This complements and completes the existing set of imidazole-based sulfonamides and sulfamides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00295-4
• 作为产物：
  描述：

  1-三苯甲基咪唑-4-甲醛 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 、 caesium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 57.0h， 生成 N-benzyl-5-(1-(triphenylmethyl)imidazol-4-yl)-1-pentanesulfonamide
  参考文献：
  名称：

  ω-(Imidazol-4-yl)alkane-1-sulfonamides: a new series of potent histamine H3 receptor antagonists

  摘要：

  omega-(1H-imidazol-4-yl)alkane-1-sulfonamides were prepared and found to be potent histamine H-3 receptor antagonists. High receptor affinity and a low difference in the data between the bioassays were achieved with 5-(1H-imidazol-4-yl)pentane-1-sulfonic acid 4-chlorobenzylamide (16). Good in vitro profiles were also obtained for 2-hydroxysulfonamide and vinylsulfonamide analogues. This complements and completes the existing set of imidazole-based sulfonamides and sulfamides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00295-4

文献信息

• 1H-4(5)-substituted imidazole derivatives, their preparation and their use as histamine H3 receptor ligands
  申请人：James Black Foundation Limited

  公开号：US06355665B1

  公开（公告）日：2002-03-12

  A compound of the formula wherein R2 is an optionally substituted Cz to Cg alkylene or alkylene chain; R3 is C2 to C15 optionally substituted hydrocarbyl; X is a bond or —NR4—, wherein R4 is hydrogen or non-aromatic C1 to C5 optionally substituted hydrocarbyl, or aryl(C1 to C3)alkyl, or a pharmaceutically acceptable salt thereof. A method of modifing histamine activity in a patient comprising administering to said patient a pharmaceutical composition containing an effective amount of a compound of formula wherein R1 is selected from C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkylthio, carboxy, carboxy(C1 to C6)alkyl, formyl, C1 to C6 alkylcarbonyl, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylamino, di(C1 to C6 alkyl)amino, aryl, C1 to C6 alkylaryl, halo, sulfamoyl and cyano; R2 is optionally substituted C2 to C20 hydrocarbylene, in which one or more hydrogen atoms may be replaced by halogen atoms and up to 6 carbon atoms may be replaced by oxygen or nitrogen atoms, R2 being in the form of an optionally substituted C2 to C8 alkylene or alkenylene chain; R3 is hydrogen or C1 to C15 optionally substituted hydrocarbyl; X is a bond or —NR4—; and a is from 0 to 2, or a pharmaceutically acceptable salt thereof.

  该化合物的化学式中，R2是一个可选取代的Cz到Cg烷基或烷基链；R3是C2到C15可选取代的烃基；X是一个键或-NR4-，其中R4是氢或非芳香C1到C5可选取代的烃基，或芳基(C1到C3)烷基，或其药学上可接受的盐。一种调节组胺在患者体内活性的方法，包括向该患者投予含有一定量该化合物的药物组合物，该化合物的化学式中，R1选自C1到C6烷基，C1到C6烷氧基，C1到C6烷硫基，羧基，羧基(C1到C6)烷基，甲酰基，C1到C6烷基羰基，C1到C6烷基羰基烷氧基，硝基，三卤甲基，羟基，氨基，C1到C6烷基羰基烷氧基，硝基，三卤甲基，羟基，氨基，C1到C6烷基氨基，二(C1到C6烷基)氨基，芳基，C1到C6烷基芳基，卤素，磺酰胺和氰基；R2是可选取代的C2到C20烃基，其中一个或多个氢原子可被卤素原子取代，最多6个碳原子可被氧原子或氮原子取代，R2以可选取代的C2到C8烷基或烯基链的形式存在；R3是氢或C1到C15可选取代的烃基；X是一个键或-NR4-；a为0到2，或其药学上可接受的盐。
• US6355665B1
  申请人：——

  公开号：US6355665B1

  公开（公告）日：2002-03-12
• [EN] 1H-4(5)-SUBSTITUTED IMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS HISTAMINE H3 RECEPTOR LIGANDS<br/>[FR] DERIVES D'IMIDAZOLE 1H-4(5)-SUBSTITUES, LEUR PREPARATION ET LEUR UTILISATION EN TANT QUE LIGANDS DU RECEPTEUR H3 DE L'HISTAMINE
  申请人：——

  公开号：WO1999005114A2

  公开（公告）日：1999-02-04

  [EN] Compounds of formula (I) wherein R<1> is selected from C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkylthio, carboxy, carboxy (C1 to C6)alkyl, formyl, C1 to C6 alkylcarbonyl, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylamino, di(C1 to C6 alkyl)amino, aryl, C1 to C6 alkylaryl, halo, sulfamoyl and cyano; R<2> is C1 to C20 hydrocarbylene, in which one or more hydrogen atoms may be replaced by halogen atoms and up to 6 carbon atoms may be replaced by oxygen, nitrogen or sulfur atoms, provided that R<2> does not contain a -O-O- group, and provided also that the atom in R<2> which is linked to the -SO2- moiety is a carbon atom; R<3> is hydrogen or C1 to C15 hydrocarbyl, in which one or more hydrogen atoms may be replaced by halogen atoms and up to 3 carbon atoms may be replaced by oxygen, nitrogen or sulfur atoms, provided that R<3> does not contain a -O-O- group; X is a bond or -NR<4>-, wherein R<4> is hydrogen or non-aromatic C1 to C5 hydrocarbyl (in which one or more hydrogen atoms may be replaced by halogen atoms and up to 2 carbon atoms may be replaced by oxygen, nitrogen or sulfur atoms, provided that R<4> does not contain a -O-O- group), aryl(C1 to C3)alkyl or R<4> represents a bond to R<2>; and a is from 0 to 2, and their pharmaceutically acceptable salts are useful as histamine H3 receptor ligands.
  [FR] L'invention se rapporte à des composés représentés par la formule (I) et à leurs sels pharmaceutiquement acceptables qui s'avèrent utiles en tant que ligands du récepteur H<3> de l'histamine. Dans la formule (I), R<1> est sélectionné parmi les groupes C1-C6 alkyle, C1-C6 alcoxy, C1-C6 alkylthio, C1-C6 alkylthio, C1-C6 carboxy, carboxy-C1-C6-alkyle, formyle, C1-C6 alkylcarbonyle, C1-C6 alkylcarbonylalcoxy, nitro, trihalométhyle, hydroxy, amino, C1-C6 alkylamino, di(alkyle C1-C6)amino, aryle, C1-C6 alkylaryle, halo, sulfanoyle et cyano; R<2> est C1-C20 hydrocarbylène, dans lequel un ou plusieurs atomes d'hydrogène peuvent être remplacés par des atomes d'halogène et jusqu'à 6 atomes de carbone peuvent être remplacés par des atomes d'oxygène, d'azote ou de soufre, à condition que R<2>, ne contienne pas de groupe -O-O-, et que l'atome de R<2> qui est lié à la fraction -SO2- soit un atome de carbone; R<3> est hydrogène ou C1-C15 hydrocarbyle, dans lequel un ou plusieurs atomes d'hydrogène peuvent être remplacés par des atomes d'halogène, d'azote ou de soufre, à condition que R<3> ne contienne pas de groupe -O-O-; X représente une liaison ou -NR<4>-, où R<4> est hydrogène ou C1-C5 hydrocarbyle non aromatique (dans lequel un ou plusieurs atomes d'hydrogène ne peuvent être remplacés par des atomes d'halogène, et jusqu'à 2 atomes de carbone peuvent être remplacés par des atomes d'oxygène, d'azote, ou de soufre, à condition que R<4> ne contienne pas de groupe -O-O-), aryle-(C1-C3)-alkyle C1-C3, ou R<4> représente une liaison avec R<2>; et a est compris entre 0 et 2.
• ω-(Imidazol-4-yl)alkane-1-sulfonamides: a new series of potent histamine H3 receptor antagonists
  作者：Matthew J. Tozer、Ildiko M. Buck、Tracey Cooke、S.Barret Kalindjian、Michael J. Pether、Katherine I.M. Steel

  DOI：10.1016/s0968-0896(01)00295-4

  日期：2002.2

  omega-(1H-imidazol-4-yl)alkane-1-sulfonamides were prepared and found to be potent histamine H-3 receptor antagonists. High receptor affinity and a low difference in the data between the bioassays were achieved with 5-(1H-imidazol-4-yl)pentane-1-sulfonic acid 4-chlorobenzylamide (16). Good in vitro profiles were also obtained for 2-hydroxysulfonamide and vinylsulfonamide analogues. This complements and completes the existing set of imidazole-based sulfonamides and sulfamides. (C) 2001 Elsevier Science Ltd. All rights reserved.