4-methyl-N-(4-methylphenethyl)benzamide

• 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-methyl-N-(4-methylphenethyl)benzamide
• 英文别名: 4-methyl-N-[2-(4-methylphenyl)ethyl]benzamide
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: ICLWABXUNBIHHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对甲基苯甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 4-methyl-N-(4-methylphenethyl)benzamide
  参考文献：
  名称：

  Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest

  摘要：

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.

  DOI：

  10.1021/ja042913p

文献信息

• Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides
  作者：Ayushee、Monika Patel、Priyanka Meena、Kousar Jahan、Prasad V. Bharatam、Akhilesh K. Verma

  DOI：10.1021/acs.orglett.0c04084

  日期：2021.1.15

  anti-Markovnikov hydroamidation of vinyl arenes with arylamides to furnish the arylethylbenzamides with excellent chemo- and regioselectivity. The reaction tolerates an extensive variety of functional groups and has been successfully extended with electronically varied handles, aminobenzamides, electron-rich/electron-deficient heterocyclic amides, and vinyl arenes to afford the hydroamidated products.

  我们研究了乙烯基芳烃与芳基酰胺的分子间抗Markovnikov加氢酰胺化的碱促进方案，以提供具有优异的化学和区域选择性的芳基乙基苯甲酰胺。该反应可耐受多种官能团，并已成功地扩展了电子形式的手柄，氨基苯甲酰胺，富电子/缺电子的杂环酰胺和乙烯基芳烃，以提供加氢酰胺化产物。观察到酰胺基优于胺具有出色的化学选择性。氘标记研究和对照实验充分支持了所提出的溶剂机理和重要作用。
• [EN] COMPOUNDS AND METHODS FOR TREATMENT OF CANCER AND MODULATION OF PROGRAMMED CELL DEATH FOR MELANOMA AND OTHER CANCER CELLS<br/>[FR] COMPOSES ET PROCEDES DE TRAITEMENT DU CANCER ET MODULATION DE LA MORT CELLULAIRE PROGRAMMEE DE MELANOMES ET D'AUTRES CELLULES CANCEREUSES
  申请人：UNIV ALABAMA

  公开号：WO2005044191A3

  公开（公告）日：2005-10-20
• [EN] COMBINATION OF AN H3 ANTAGONIST/INVERSE AGONIST AND AN APPETITE SUPPRESSANT<br/>[FR] COMBINAISON D'UN ANTAGONISTE/AGONISTE INVERSE DE H3 ET D'UN MODERATEUR DE L'APPETIT
  申请人：SCHERING CORP

  公开号：WO2007075555A2

  公开（公告）日：2007-07-05

  [EN] The present invention relates to pharmaceutical compositions comprising therapeutic combinations comprising: one or more H3 antagonists/inverse agonists; one or more appetite suppressants selected from the group consisting of CBi antagonists/inverse agonists, sibutramine, phentermine and topiramate; and option one or more HMG-CoA reductase inhibitors. The invention also relates to medicaments and kits comprising the pharmaceutical compositions of the present invention, and methods of treating obesity, obesity related disorders and diabetes using the pharmaceutical compositions of the present invention.
  [FR] La présente invention concerne des compositions pharmaceutiques comprenant les combinaisons thérapeutiques suivantes : un ou plusieurs antagonistes/agonistes inverses de H3 ; un ou plusieurs modérateurs de l'appétit choisis dans le groupe comprenant des antagonistes/agonistes inverses de CBi, la sibutramine, la phentermine et le topiramate ; et facultativement un ou plusieurs inhibiteurs de la HMG-CoA réductase. L'invention concerne également des médicaments et des kits comprenant les compositions pharmaceutiques de la présente invention et des procédés de traitement de l'obésité, des troubles liés à l'obésité et du diabète à l'aide des compositions pharmaceutiques de la présente invention.
• Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest
  作者：Robin S. Dothager、Karson S. Putt、Brittany J. Allen、Benjamin J. Leslie、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja042913p

  日期：2005.6.1

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.