4-[Phenyl(propyl)sulfamoyl]benzoic acid | 918666-95-2

• 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-[Phenyl(propyl)sulfamoyl]benzoic acid
• CAS: 918666-95-2
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: RAKUKGYCCSDBHH-UHFFFAOYSA-N

物化性质

• 沸点：
  496.1±47.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[Phenyl(propyl)sulfamoyl]benzoic acid 反应 3.0h， 生成 5-Iodo-2-[[4-[phenyl(propyl)sulfamoyl]benzoyl]amino]benzoic acid
  参考文献：
  名称：

  Discovery and initial development of a novel class of antibacterials: Inhibitors of Staphylococcus aureus transcription/translation

  摘要：

  The novel bacterial transcription/translation (TT) inhibitor 1 was identified through a combination of high throughput screening and exploratory medicinal chemistry. Initial optimization of the anthranilic acid moiety and sulfonamide amine diversity was accomplished via 1- and two-dimensional solution phase libraries, resulting in an improvement in the MIC of the lead from 64 to 8 mu g/mL (compound 4I). Subsequent modification of the central aromatic ring and further refinement of the sulfonamide amines required the development of a solid phase route on Wang resin. The resulting libraries generated a number of potent antibacterials with MICs of <= 1 mu g/mL (e.g., 10b, 12, and 13). During the course of this work, it became apparent that the antibacterial activity of the series is not fully correlated with TT inhibition, suggesting that at least one additional mechanism of action is operative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.044
• 作为产物：
  描述：

  4-(氯磺酰)苯甲酸 、 N-丙基苯胺 以 甲醇 为溶剂， 反应 3.0h， 生成 4-[Phenyl(propyl)sulfamoyl]benzoic acid
  参考文献：
  名称：

  Discovery and initial development of a novel class of antibacterials: Inhibitors of Staphylococcus aureus transcription/translation

  摘要：

  The novel bacterial transcription/translation (TT) inhibitor 1 was identified through a combination of high throughput screening and exploratory medicinal chemistry. Initial optimization of the anthranilic acid moiety and sulfonamide amine diversity was accomplished via 1- and two-dimensional solution phase libraries, resulting in an improvement in the MIC of the lead from 64 to 8 mu g/mL (compound 4I). Subsequent modification of the central aromatic ring and further refinement of the sulfonamide amines required the development of a solid phase route on Wang resin. The resulting libraries generated a number of potent antibacterials with MICs of <= 1 mu g/mL (e.g., 10b, 12, and 13). During the course of this work, it became apparent that the antibacterial activity of the series is not fully correlated with TT inhibition, suggesting that at least one additional mechanism of action is operative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.044

文献信息

• AMINOSULPHONYLBENZAMIDE DERIVATIVES AS MODULATORS OF THE ACTIVITY OF NEURONAL CALCIUM CHANNELS
  申请人：ELI LILLY AND COMPANY LIMITED

  公开号：EP1047670A1

  公开（公告）日：2000-11-02
• [EN] AMINOSULPHONYLBENZAMIDE DERIVATIVES AS MODULATORS OF THE ACTIVITY OF NEURONAL CALCIUM CHANNELS<br/>[FR] DERIVES AMINOSULPHONYLBENZAMIDES UTILISES COMME INHIBITEURS DE L'ACTIVITE DES CANAUX CALCIUM NEURONAUX
  申请人：ELI LILLY AND COMPANY LIMITED

  公开号：WO1999036398A1

  公开（公告）日：1999-07-22

  (EN) A pharmaceutical compound of formula (I) in which the aminosulfonyl group is attached at the 3- or 4-position, and in which R1 is hydrogen, C1-6 Alkyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-4 alkyl or optionally substituted phenyl-C1-4 alkyl, R2 is C1-6 alkyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-4 alkyl, optionally substituted phenyl-C1-4 alkyl or -(CH2)2NR5R6 where R5 and R6 are each hydrogen or C1-6 alkyl, and R3 and R4 are each C1-6 alkyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-4 alkyl, C3-6 alkenyl, optionally substituted phenyl or optionally substituted phenyl-C1-4 alkyl, or R1 and R2, or R3 and R4, or R5 and R6, together with the nitrogen atom to which they are attached, form a carbocyclic group containing 4 to 7 carbon atoms optionally substituted with one to three methyl or ethyl groups and optionally containing an oxygen atom or a further nitrogen atom, said carbocyclic group being optionally fused to an optionally substituted phenyl group; or a salt thereof.(FR) L'invention se rapporte à un composé pharmaceutique représenté par la formule (I) dans laquelle le groupe aminosulfonyle est attaché en position 3 ou 4 et où R1 est hydrogène, alkyle C1-C6, cycloalkyle C3-C10, cycloalkyle C3-C10-alkyle C1-C4 ou phényle-alkyle C1-C4, R2 est alkyle C1-C6, cycloalkyle C3-C10, cycloalkyle C3-C10-alkyle C1-C4 ou phényle-alkyle C1-C4 ou (CH2)2NR5R6 où R5 et R6 sont chacun hydrogène ou alkyle C1-C6, et R3 et R4 sont chacun alkyle C1-C6, cycloalkyle C3-C10, cycloalkyle C3-C10-alkyle C1-C4, alcényle C3-C6, phényle éventuellement substitué ou phényle-alkyle C1-C4 éventuellement substitué, ou bien R1 et R2, ou R3 et R4, ou R5 et R6 forment conjointement à l'atome d'azote auquel ils sont attachés, un groupe carbocyclique contenant 4 à 7 atomes de carbone éventuellement substitués par un à trois groupes méthyle ou éthyle et contenant éventuellement un atome d'oxygène ou un autre atome d'azote, ledit groupe carbocyclique étant éventuellement fusionné à un groupe phényle éventuellement substitué. L'invention se rapporte également à un sel de ce composé.
• Discovery and initial development of a novel class of antibacterials: Inhibitors of Staphylococcus aureus transcription/translation
  作者：Scott D. Larsen、Matthew R. Hester、J. Craig Ruble、Gregg M. Kamilar、Donna L. Romero、Brian Wakefield、Earline P. Melchior、Michael T. Sweeney、Keith R. Marotti

  DOI：10.1016/j.bmcl.2006.09.044

  日期：2006.12

  The novel bacterial transcription/translation (TT) inhibitor 1 was identified through a combination of high throughput screening and exploratory medicinal chemistry. Initial optimization of the anthranilic acid moiety and sulfonamide amine diversity was accomplished via 1- and two-dimensional solution phase libraries, resulting in an improvement in the MIC of the lead from 64 to 8 mu g/mL (compound 4I). Subsequent modification of the central aromatic ring and further refinement of the sulfonamide amines required the development of a solid phase route on Wang resin. The resulting libraries generated a number of potent antibacterials with MICs of <= 1 mu g/mL (e.g., 10b, 12, and 13). During the course of this work, it became apparent that the antibacterial activity of the series is not fully correlated with TT inhibition, suggesting that at least one additional mechanism of action is operative. (c) 2006 Elsevier Ltd. All rights reserved.