2-氨基-1-苯并[1,3]二氧代-5-乙酮盐酸盐 | 38061-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 2-氨基-1-苯并[1,3]二氧代-5-乙酮盐酸盐
• 英文名称: 2-amino-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one hydrochloride
• 英文别名: 2-amino-1-benzo[1,3]dioxol-5-yl-ethanone; hydrochloride；2-Amino-1-benzo[1,3]dioxol-5-yl-aethanon; Hydrochlorid；2-amino-3',4'-methylenedioxyacetophenone hydrochloride；2-(2h-1,3-Benzodioxol-5-yl)-2-oxoethan-1-aminium chloride；[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]azanium;chloride
• CAS: 38061-34-6
• 化学式: C₉H₉NO₃*ClH
• 分子量: 215.636
• InChiKey: XXHCAYKHYVJABF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-氨基-1-苯并[1,3]二氧代-5-乙酮盐酸盐 在 四(三苯基膦)钯 、 正丁基锂 、 1,3-二甲基巴比妥酸 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 6.75h， 生成
  参考文献：
  名称：

  Discovery and Characterization of a Highly Potent and Selective Aminopyrazoline-Based in Vivo Probe (BAY-598) for the Protein Lysine Methyltransferase SMYD2

  摘要：

  Protein lysine methyltransferases have recently emerged as a new target class for the development of inhibitors that modulate gene transcription or signaling pathways. SET and MYND domain containing protein 2 (SMYD2) is a catalytic SET domain containing methyltransferase reported to monomethylate lysine residues on histone and nonhistone proteins. Although several studies have uncovered an important role of SMYD2 in promoting cancer by protein methylation, the biology of SMYD2 is far from being fully understood. Utilisation of highly potent and selective chemical probes for target validation has emerged as a concept which circumvents possible limitations of knockdown experiments and, in particular, could result in an improved exploration of drug targets with a complex underlying biology. Here, we report the development of a potent, selective, and cell-active, substrate-competitive inhibitor of SMYD2, which is the first reported inhibitor suitable for in vivo target validation studies in rodents.

  DOI：

  10.1021/acs.jmedchem.5b01890
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 氢气 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 二甲基亚砜 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 2-氨基-1-苯并[1,3]二氧代-5-乙酮盐酸盐
  参考文献：
  名称：

  Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline

  摘要：

  Texaline, an antimycobacterial oxazole-containing alkaloid previously isolated from Amyris texana and A. elemifera, and related compounds have been synthesized in order to explore aspects of the structure-anti tuberculosis activity relationship. While texaline was found to be inactive in our assays, simpler diaryloxazoles were more active whilst also exhibiting modest toxic selectivity, leading to their identification as potential lead compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.119

文献信息

• [EN] ANTIBACTERIAL BENZOIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDES BENZOIQUES ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004018428A1

  公开（公告）日：2004-03-04

  The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.

  这项发明提供了抗菌剂和使用这些剂进行哺乳动物的消毒、卫生、防腐、消毒和治疗感染的方法。
• Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy
  作者：Bo Kong、Zhaohong Zhu、Hongmei Li、Qianqian Hong、Cong Wang、Yu Ma、Wan Zheng、Fei Jiang、Zhimin Zhang、Ting Ran、Yuanyuan Bian、Na Yang、Tao Lu、Jiapeng Zhu、Weifang Tang、Yadong Chen

  DOI：10.1016/j.ejmech.2021.113953

  日期：2022.1

  modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic

  作为表观遗传阅读器，溴结构域和末端外结构域 (BET) 家族蛋白与组蛋白中的乙酰化赖氨酸残基结合并募集蛋白质复合物以促进转录起始和延伸。通过小分子抑制剂抑制 BET 溴结构域已成为一种有前途的癌症治疗策略。在这里，我们描述了我们为发现一系列新的 1-(5-(1 H -benzo[ d ]imidazole-2-yl)-2,4-dimethyl-1 H -pyrrol-3-yl)ethan 所做的努力-1-one 衍生物作为 BET 抑制剂。密集的结构修饰导致化合物35f被鉴定为对 BET 家族蛋白具有选择性的最活跃的 BET BRD4 抑制剂。进一步的生物学研究表明，化合物35f通过降低c-Myc等细胞周期和细胞凋亡相关蛋白的表达，使细胞周期停滞在G 0 /G 1期，诱导细胞凋亡。更重要的是，化合物35f在 MV4-11 小鼠异种移植模型中显示出良好的药代动力学特性和抗肿瘤功效，具有可接受的耐受性。这些结果表明，BET
• Iodine-Promoted Oxidative Cyclization of Methyl Azaarenes and α-Amino Ketones for One-Pot Synthesis of 2-Azaaryl-5-aryl Oxazoles
  作者：Yan-Ping Zhu、Yu Zhou、Wen-Juan Li、Fu-Rao Liu、Wen-Cheng Wang、Kai-Yan Hao、Bing-Yu Chao、Tian-Ru Shi、An-Xin Wu、Yuan-Yuan Sun

  DOI：10.1021/acs.joc.2c01399

  日期：2022.9.16

  the synthesis of 2,5-disubstituted oxazoles via iodine-promoted oxidative domino cyclization. These reactions were performed with readily available methyl azaarenes and α-amino ketones under metal-free conditions. This protocol is a simple method with high functional group compatibility, a wide range of substrates, and excellent yield, providing a new way to synthesize azaarene-attached oxazoles.

  开发了一种通过碘促进的氧化多米诺环化合成 2,5-二取代恶唑的高效方案。这些反应是在无金属条件下使用容易获得的甲基氮杂芳烃和 α-氨基酮进行的。该方案是一种简单的方法，具有高官能团相容性、广泛的底物和优异的产率，为合成氮杂芳烃附着恶唑提供了新的途径。
• Alkylation of .alpha.-formamido ketone enolate anions. A versatile synthesis of .alpha.-alkyl .alpha.-amino ketones
  作者：Jack Ackrell、Joseph M. Muchowski、Edvige Galeazzi、Angel Guzman

  DOI：10.1021/jo00367a026

  日期：1986.8
• ACKRELL J.; MUCHOWSKI J. M.; GALEAZZI E.; GUZMAN A., J. ORG. CHEM., 51,(1986) N 17, 3374-3376
  作者：ACKRELL J.、 MUCHOWSKI J. M.、 GALEAZZI E.、 GUZMAN A.

  DOI：——

  日期：——