1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine

• 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: 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine
• 英文别名: 1-((4-(Bromomethyl)phenyl)sulfonyl)-4-methylpiperidine；1-[4-(bromomethyl)phenyl]sulfonyl-4-methylpiperidine
• 化学式: C₁₃H₁₈BrNO₂S
• 分子量: 332.261
• InChiKey: HHZNBHOYACMMJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine 、 5-(2,4-二氯苯基)-1,3,4-噁二唑-2(3h)-硫酮 在 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80%的产率得到1-[4-({[5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl]thio}methyl)benzenesulfonyl]-4-methylpiperidine
  参考文献：
  名称：

  SYNTHESIS, SPECTRAL ANALYSIS AND ANTIBACTERIAL EVALUATION OF 5-SUBSTITUTED-1,3,4-OXADIAZOL-2-YL 4-(4-METHYLPIPERIDIN-1-YLSULFONYL)BENZYL SULFIDES

  摘要：

  Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio] methyl} benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4- methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, H-1-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.

  DOI：

  10.4067/s0717-97072017000100013
• 作为产物：
  描述：

  4-甲基哌啶 、 4-溴甲基苯磺酰氯 在 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine
  参考文献：
  名称：

  SYNTHESIS, SPECTRAL ANALYSIS AND ANTIBACTERIAL EVALUATION OF 5-SUBSTITUTED-1,3,4-OXADIAZOL-2-YL 4-(4-METHYLPIPERIDIN-1-YLSULFONYL)BENZYL SULFIDES

  摘要：

  Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio] methyl} benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4- methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, H-1-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.

  DOI：

  10.4067/s0717-97072017000100013

文献信息

• Fused pyrimidinone matrix metalloproteinase inhibitors
  申请人：——

  公开号：US20030004172A1

  公开（公告）日：2003-01-02

  Selective MMP-13 inhibitors are fused pyrimidinones of the formula 1 or a pharmaceutically acceptable salt thereof, wherein: W, together with the carbon atoms to which it is attached, form a 5-membered ring diradical 2 X is O, S, SO, SO 2 , NR 5 , or CH 2 ; 3 B is O or NR 5 ; or A and B are taken together to form —C≡C—; R 1 , R 4 , and R 5 are hydrogen, alkyl, alkenyl, alkynyl, (CH 2 ) n aryl, (CH 2 ) n cycloalkyl, C 1 -C 6 alkanoyl, or (CH 2 ) n heteroaryl; R 2 and R 3 are hydrogen, alkyl, alkenyl, alkynyl CN, NO 2 , NR 4 R 5 , (CH 2 ) n cycloalkyl, (CH 2 ) n aryl, or (CH 2 ) n heteroaryl; R 2 may further be halo; n is an integer of from 0 to 5; and R 4 and R 5 when taken together with a nitrogen to which they are both attached complete a 3- to 8-membered ring containing carbon atoms and optionally containing O, S, or N, and substituted or unsubstituted; with the proviso that R 1 and R 3 are not both selected from hydrogen and C 1 -C 6 alkyl.

  选择性MMP-13抑制剂是具有以下结构的嘧啶酮类化合物或其药用盐： 其中： W与其连接的碳原子一起形成一个5元环二自由基； X为O、S、SO、SO2、NR5或CH2； B为O或NR5； 或A和B结合形成—C≡C—； R1、R4和R5为氢、烷基、烯基、炔基、(CH2)n芳基、(CH2)n环烷基、C1-C6烷酰基或(CH2)n杂环芳基； R2和R3为氢、烷基、烯基、炔基、CN、NO2、NR4R5、(CH2)n环烷基、(CH2)n芳基或(CH2)n杂环芳基；R2还可以是卤素； n为0到5的整数； R4和R5与它们都连接的氮一起形成含碳原子且可选择含有O、S或N的3-8元环，可以是取代或未取代的； 但要注意R1和R3不同时选择自氢和C1-C6烷基。
• THIENO[2,3-D]PYRIMIDINDIONE DERIVATIVES AS MATRIX METALLOPROTEINASE INHIBITORS
  申请人：Warner-Lambert Company LLC

  公开号：EP1370562A1

  公开（公告）日：2003-12-17
• [EN] THIENO'2,3-D PYRIMIDINDIONE DERIVATIVES AS MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] DERIVES DE THIENO'2,3-D PYRIMIDINONE UTILISES COMME INHIBITEURS DE METALLOPROTEINASES MATRICIELLES
  申请人：WARNER LAMBERT CO

  公开号：WO2002064598A1

  公开（公告）日：2002-08-22

  Selective MMP-13 inhibitors are fused pyrimidinones of the formula or a pharmaceutically acceptable salt thereof, wherein: W, together with the carbon atoms to which it is attached, form a 5-membered ring diradical Y is O, S, SO, SO2, NR5, or CH¿2, ?A is-C-or S-; B is O or NR?5¿; or A and B are taken together to form -C C-; R?1, R4, and R5¿ are hydrogen, alkyl, alkenyl, alkynyl, (CH¿2?)n aryl, (CH2)n cycloalkyl, C1 C6 alkanoyl, or (CH2)n heteroaryl; R?2 and R3¿ are hydrogen, alkyl, alkenyl, alkynyl CN, NO¿2?, NR?4R5, (CH¿2)n cycloalkyl, (CH2)n aryl, or (CH2)n heteroaryl; R2 may further be halo; n is an integer of from 0 to 5; and R?4 and R5¿ when taken together with the nitrogen to which they are attached complete a 3-to 8-membered ring containing carbon atoms and optionally containing O, S, or N, and substituted or unsubstituted; with the proviso that R?1 and R3¿ are not both selected from hydrogen and C¿1-?C6 alkyl.
• SYNTHESIS, SPECTRAL ANALYSIS AND ANTIBACTERIAL EVALUATION OF 5-SUBSTITUTED-1,3,4-OXADIAZOL-2-YL 4-(4-METHYLPIPERIDIN-1-YLSULFONYL)BENZYL SULFIDES
  作者：AZIZ-UR-REHMAN、SAMREEN AHTZAZ、MUHAMMAD ATHAR ABBASI、SABAHAT ZAHRA SIDDIQUI、SHAHID RASOOL、IRSHAD AHMAD

  DOI：10.4067/s0717-97072017000100013

  日期：——

  Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-[(5-substituted-1,3,4-oxadiazol-2-yl) thio] methyl} benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4- methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, H-1-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.
• Synthesis of Bi-Heterocyclic Sulfonamides as Tyrosinase Inhibitors: Lineweaver–Burk Plot Evaluation and Computational Ascriptions
  作者：Muhammad Athar Abbasi、Zia-ur Rehman、Aziz-ur Rehman、Sabahat Zahra Siddiqui、Majid Nazir、Mubashir Hassan、Hussain Raza、Syed Adnan Ali Shah、Sung-Yum Seo

  DOI：10.17344/acsi.2019.5283

  日期：——

  The designed bi-heterocyclic sulfonamides were synthesized through a two-step protocol and their structures were ascertained by spectral techniques including IR, H-1 NMR and C-13 NMR along with CHN analysis. The in vitro inhibitory effects of these sulfonamides were evaluated against tyrosinase and kinetics mechanism was analyzed by LineweaverBurk plots. The binding modes of these molecules were ascribed through molecular docking studies. These synthesized bi-heterocyclic molecules were identified as potent inhibitors relative to the standard (kojic acid) and compound 5 inhibited the tyrosinase non-competitively by forming an enzyme-inhibitor complex. The inhibition constant Ki (0.09 mu M) for compound 5 was calculated from Dixon plots. Computational results also displayed that all compounds possessed good binding profile against tyrosinase and interacted with core residues of target protein.