methyl 4-(prop-2-yn-1-ylcarbamoyl)benzoate | 111194-78-6

• 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: methyl 4-(prop-2-yn-1-ylcarbamoyl)benzoate
• 英文别名: Methyl 4-[(2-propynylamino)carbonyl]benzoate；methyl 4-(prop-2-ynylcarbamoyl)benzoate
• CAS: 111194-78-6
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: UNFTVOUFMOMPTK-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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(prop-2-yn-1-ylcarbamoyl)benzoate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以97.2%的产率得到4-(prop-2-yn-1-ylcarbamoyl)benzoic acid
  参考文献：
  名称：

  Discovery of 4-benzoylamino-N-(prop-2-yn-1-yl)benzamides as novel microRNA-21 inhibitors

  摘要：

  MicroRNA-21, as an oncogenic miRNA, has caught great attention for medicinal chemists to develop its novel inhibitors for cancer therapy. In the present study, we designed 4-benzoylamino-N-(prop-2-yn-1-yl) benzamides as miR-21 inhibitor candidates on the basis of scaffold hopping. Eighteen compounds were synthesized. The inhibitory activities of synthesized compounds against the expression of miR-21 were evaluated using stem loop RT-qPCR and compound 1j was discovered as the most potent compound, which displayed a time and concentration dependent inhibition manner. In addition, various functional assays such as the expression of miR-21 target gene detected by Western blotting and the cell growth and apoptosis detected by flow cytometric analysis were checked in Hela (human epithelioid cervix carcinoma) and U-87 MG (human glioblastoma) cells to confirm its activity. The results indicate that compound 1j can enhance apoptosis, retard proliferation, and up-regulate PDCD4, a target protein of miR-21. In addition, the compound 1j does not influence the expression of multiple miRNAs and the genes that participate in miRNA universal biosynthesis pathway. These results strongly support the assumption that title compounds can serve as a small molecule inhibitor of miR-21. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.007
• 作为产物：
  描述：

  4-氯甲酰基苯甲酸甲酯 在 1,3-二氯-5,5-二甲基海因 、 bis(η3-allyl-μ-chloropalladium(II)) 、 磷酸三乙酯 、 柠檬酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 methyl 4-(prop-2-yn-1-ylcarbamoyl)benzoate
  参考文献：
  名称：

  酸性水溶液条件下胺与酰基硅烷的化学选择性 N-酰化

  摘要：

  我们报道了一种在酸性水溶液条件下，在温和氯化剂存在下，在酰基硅烷和多种胺之间形成酰胺键的简便方法。该反应具有高度化学选择性，一组已批准的药物和含有反应性功能的天然产物的后期修饰就是例证。

  DOI：

  10.1021/acs.orglett.3c01911

文献信息

• Palladium-Catalyzed Cascade Difluoroalkylation/Cyclization of <i>N</i>-Propargylamides: Synthesis of Oxazoles and Oxazolines
  作者：Jun-Wei Ma、Qiang Wang、Xin-Gang Wang、Yong-Min Liang

  DOI：10.1021/acs.joc.8b02111

  日期：2018.11.2

  A palladium-catalyzed process to construct oxazoles and oxazolines with broad functional-group tolerance has been developed, and the method introduces difluoromethyl groups into heterocycles in a one-pot fashion. This system uses a carbonyl oxygen as the acceptor for the addition of a vinylpalladium intermediate to achieve the cyclization. Oxazoline derivatives are generated as the Z-isomer with high

  已经开发了钯催化的方法来构建具有宽泛的官能团耐受性的恶唑和恶唑啉，并且该方法以一锅法将二氟甲基引入杂环中。该系统使用羰基氧作为受体，以添加乙烯基钯中间体以实现环化。恶唑啉衍生物以高立体选择性的Z-异构体形式产生。此外，我们验证了该反应的初步机制。
• Efficient synthesis of N-(buta-2,3-dienyl) amides from terminal N-propargyl amides and their synthetic potential towards oxazoline derivatives
  作者：Bo Chen、Nan Wang、Wu Fan、Shengming Ma

  DOI：10.1039/c2ob26291f

  日期：——

  A series of N-allenyl amides was prepared conveniently from N-propargyl amides in good to excellent yields via a modified procedure developed in this group. The palladium-catalyzed coupling–cyclization of these prepared N-allenyl amides in the presence of organic iodides has been developed affording the oxazoline derivatives efficiently.

  一系列Ñ -allenyl酰胺被方便地从制备Ñ -propargyl以良好至优异的产率的酰胺通过该组中开发了一种改进的方法。已经开发了在有机碘化物存在下这些制备的N-烯丙基酰胺的钯催化偶联-环化反应，从而有效地提供了恶唑啉衍生物。
• Synthesis of Difluoroalkyl Unsaturated β-Amino Acid Derivatives Exclusively through Alkyne Difunctionalization
  作者：Qiang Wang、Jia-Ni Jin、Xi Chen、Xin-Gang Wang、Bo-Sheng Zhang、Jun-Wei Ma、Yong-Min Liang

  DOI：10.1021/acs.joc.8b02440

  日期：2018.12.7

  Alkynes difunctionalization is a powerful strategy in organic synthesis that provides a convenient synthetic entry for internal alkenes. The main challenge in this field was considered to be the geometry control of the newly formed double bond (thermodynamically controlled or kinetically controlled). Herein, we report a novel procedure (through the cyclic compounds broken) to completely control the

  炔烃双官能化是有机合成中的强大策略，可为内部烯烃提供方便的合成入口。该领域的主要挑战被认为是新形成的双键的几何控制（热力学控制或动力学控制）。在本文中，我们报道了一种新颖的方法（通过环状化合物的断裂）来完全控制烯烃的区域选择性。由于氟原子的特殊性质，该产物二氟烷基不饱和β-氨基酸衍生物在一些重要的药物中具有潜在的应用。
• Gold‐Catalyzed One‐Pot Synthesis of Polyfluoroalkylated Oxazoles from N‐Propargylamides Under Visible‐Light Irradiation
  作者：Yantao Liu、Yating Shi、Lanen Wei、Ke Zhao、Jingjing Zhao、Puyu Zhang、Xuejun Xu、Pan Li

  DOI：10.1002/asia.202100614

  日期：2021.9

  one-pot rapid synthesis of polyfluoroalkylated oxazoles from N-propargylamides under visible light irradiation has been developed. The current protocol displays excellent compatibility of radicals and gold catalysts, affording polyfluoroalkylated oxazoles in decent yields with good functional group compatibility under mild conditions.

  已开发出在可见光照射下从 N-炔丙基酰胺中金催化一锅法快速合成多氟烷基化恶唑。目前的协议显示出自由基和金催化剂的优异相容性，在温和的条件下以良好的收率提供多氟烷基化恶唑，并具有良好的官能团兼容性。
• Indole derivatives
  申请人：Glaxo Group Limited

  公开号：US04855314A1

  公开（公告）日：1989-08-08

  Compounds are disclosed of formula (I): ##STR1## wherein R.sub.1 is halogen, a C.sub.1-3 alkoxy, R.sub.6 R.sub.7 NCO(CH.sub.2).sub.p --, R.sub.6 CONH(CH.sub.2).sub.p --, R.sub.6 R.sub.7 NSO.sub.2 (CH.sub.2).sub.p --, or R.sub.8 SO.sub.2 NH(CH.sub.2).sub.p -- (where R.sub.6 and R.sub.7 each represents hydrogen or C.sub.1-3 alkyl, R.sub.8 represents C.sub.1-3 alkyl and p is zero or 1); R.sub.2 represents hydrogen or C.sub.1-3 alkyl; R.sub.3 represents hydrogen or C.sub.1-3 alkyl; R.sub.4 and R.sub.5 each represents hydrogen, C.sub.1-3 alkyl or 2-propenyl; A represents --CO-- or --SO.sub.2 --; n represents an integer from 2 to 5; and m represents zero or an integer from 1 to 4; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds have potent and selective vasoconstrictor activity and are indicated as useful for the treatment of migraine. The compounds may be formulated as pharmaceutical compositions with physiologically acceptable carriers or excipients for administration by any convenient route. Various methods for the preparation of the compounds (I) are disclosed.

  公式（I）的化合物被揭示，其中R1为卤素，C1-3烷氧基，R6R7NCO（CH2）p--，R6CONH（ ）p--，R6R7NSO2（ ）p--或R8SO2NH（ ）p--（其中R6和R7分别表示氢或C1-3烷基，R8表示C1-3烷基，p为零或1）；R2表示氢或C1-3烷基；R3表示氢或C1-3烷基；R4和R5分别表示氢，C1-3烷基或2-丙烯基；A表示--CO--或--SO2--；n表示从2到5的整数；m表示零或从1到4的整数；以及其生理上可接受的盐和溶剂（例如水合物）。这些化合物具有强效和选择性的血管收缩作用，并被指示用于治疗偏头痛。这些化合物可以与生理上可接受的载体或赋形剂一起制成药物组成物，以便通过任何方便的途径进行给药。还揭示了制备化合物（I）的各种方法。