1-(4-Methylbenzoyl)piperidin-4-one | 145729-25-5

• 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-Methylbenzoyl)piperidin-4-one
• CAS: 145729-25-5
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD09938276
• 分子量: 217.268
• InChiKey: SYWXLNAOEXIDMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Methylbenzoyl)piperidin-4-one 在 sodium hydride 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 N-(4-hydroxy-6-(4-methylbenzoyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-4-nitrobenzamide
  参考文献：
  名称：

  Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

  摘要：

  A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.007
• 作为产物：
  描述：

  4-哌啶酮 、 对甲基苯甲酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-Methylbenzoyl)piperidin-4-one
  参考文献：
  名称：

  Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

  摘要：

  A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.007

文献信息

• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Weinstein David S.

  公开号：US20090075995A1

  公开（公告）日：2009-03-19

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including inflammatory and immune diseases, having the structure of formula (I): an enantiomer, diastereomer, or tautomer thereof, or a prodrug ester thereof, or a pharmaceutically-acceptable salt thereof, in which: Z is heterocyclo or heteroaryl; A is a 5- to 8-membered carbocyclic ring or a 5- to 8-membered heterocyclic ring; B is a cycloalkyl, cycloalkenyl, aryl, heterocyclo, or heteroaryl ring, wherein each ring is fused to the A ring on adjacent atoms and optionally substituted by one to four groups which are the same or different and are independently selected from R 5 , R 6 , R 7 , and R 8 ; J 1 , J 2 , and J 3 are at each occurrence the same or different and are independently -A 1 QA 2 -; Q is a bond, O, S, S(O), or S(O) 2 ; A 1 and A 2 are the same or different and are at each occurrence independently selected from a bond, C 1-3 alkylene, substituted C 1-3 alkylene, C 2-4 alkenylene, and substituted C 2-4 alkenylene, provided that A 1 and A 2 are chosen so that ring A is a 5- to 8-membered carbocyclic or heterocyclic ring; R 1 to R 11 are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一系列新颖的非甾体化合物，这些化合物在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中很有用，包括炎性和免疫疾病，具有以下结构式（I）： 其对应的光学异构体、对映异构体或互变异构体，或其前药酯，或其药用可接受盐，其中： Z是杂环或杂芳基； A是一个5至8成员的碳环或一个5至8成员的杂环； B是一个环烷基、环烯基、芳基、杂环或杂芳基环，其中每个环都与A环上的相邻原子融合，并且可以选择性地被一个到四个独立选自R5、R6、R7和R8的相同或不同的组取代； J1、J2和J3每次出现时相同或不同，独立地选自-A1QA2-；Q是键、O、S、S(O)或S(O)2；A1和A2相同或不同，每次出现时独立地选自键、C1-3烷基、取代的C1-3烷基、C2-4烯基和取代的C2-4烯基，前提是A1和A2的选择使得环A是一个5至8成员的碳环或杂环； R1至R11如本文所述定义。 还提供了使用这些化合物的药物组合物和治疗炎性疾病、免疫相关疾病、肥胖和糖尿病的方法。
• [EN] NOVEL CHOLINE KINASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE CHOLINE KINASE
  申请人：ARIAD PHARMA INC

  公开号：WO2014151761A1

  公开（公告）日：2014-09-25

  This invention relates to compounds of the general formula (I): in which the variable groups are as identified herein, and to preparation and use of the compounds.

  这项发明涉及通式（I）的化合物，其中变量基团如本说明中所识别的，并涉及该化合物的制备和使用。
• Synthesis and optimization of novel allylated mono-carbonyl analogs of curcumin (MACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI) in rats
  作者：Heping Zhu、Tingting Xu、Chenyu Qiu、Beibei Wu、Yali Zhang、Lingfeng Chen、Qinqin Xia、Chenglong Li、Bin Zhou、Zhiguo Liu、Guang Liang

  DOI：10.1016/j.ejmech.2016.05.041

  日期：2016.10

  allylated mono-carbonyl analogs of curcumin (MACs) were synthesized using an appropriate synthetic route and evaluated experimentally thru the LPS-induced expression of TNF-α and IL-6. Most of the obtained compounds exhibited improved water solubility as a hydrochloride salt compared to lead molecule 8f. The most active compound 7a was effective in reducing the Wet/Dry ratio in the lungs and protein

  使用适当的合成途径合成了一系列新的姜黄素对称和不对称烯丙基化单羰基类似物（MACs），并通过LPS诱导的TNF-α和IL-6表达进行了实验评估。与铅分子8f相比，大多数获得的化合物均显示出改善的水溶性，即盐酸盐形式的盐酸盐。活性最高的化合物7a可有效降低肺部的湿/干比和支气管肺泡灌洗液中的蛋白质浓度。同时，在脂多糖（LPS）攻击后，Bea-2B细胞中7a还抑制了包括TNF-α，IL-6，IL-1β和VCAM-1在内的几种炎性细胞因子的mRNA表达。这些结果表明7a 在急性肺损伤（ALI）的临床治疗中用作抗炎药可能在治疗上有益。
• Aryl substituted imidazonaphthyridines
  申请人：Niwas Shri

  公开号：US20070219228A1

  公开（公告）日：2007-09-20

  Imidazonaphthyridine ring systems substituted with an aryl substituent, pharmaceutical compositions containing the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明公开了以芳基取代的咪唑萘啉环系统化合物、含有该化合物的制药组合物，以及将这些化合物用作免疫调节剂的方法，用于在动物体内诱导细胞因子的生物合成，并用于治疗包括病毒性和肿瘤性疾病在内的疾病。
• ARYL AND ARYLALKYLENYL SUBSTITUTED THIAZOLOQUINOLINES AND THIAZOLONAPHTHYRIDINES
  申请人：Prince B. Ryan

  公开号：US20070259907A1

  公开（公告）日：2007-11-08

  Thiazoloquinoline and thiazolonaphthyridine compounds having an aryl or arylalkylenyl substituent at the 6-, 7-, 8-, or 9-position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明公开了在6、7、8或9位具有芳基或芳基烷基取代基的噻唑喹啉和噻唑萘啶化合物、含有该化合物的制药组合物、中间体以及这些化合物作为免疫调节剂、用于调节动物细胞因子生物合成以及治疗包括病毒和肿瘤疾病的方法。