2'-amino-4',6'-dimethoxy-α-chloroacetophenone | 132257-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-amino-4',6'-dimethoxy-α-chloroacetophenone
• 英文别名: Ethanone, 1-(2-amino-4,6-dimethoxyphenyl)-2-chloro-；1-(2-amino-4,6-dimethoxyphenyl)-2-chloroethanone
• CAS: 132257-02-4
• 化学式: C₁₀H₁₂ClNO₃
• 分子量: 229.663
• InChiKey: ICGLEXBSEYOKMA-UHFFFAOYSA-N

物化性质

• 沸点：
  413.9±40.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-amino-4',6'-dimethoxy-α-chloroacetophenone 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以19%的产率得到4,6-二甲氧基吲哚
  参考文献：
  名称：

  Hall, Robin J.; Jackson, Anthony H.; Shannon, Patrick V. R., Journal of Chemical Research, Miniprint, 1990, # 10, p. 2501 - 2519

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 2'-amino-4',6'-dimethoxy-α-chloroacetophenone
  参考文献：
  名称：

  2-Arylidenedihydroindole-3-ones: Design, synthesis, and biological activity on bladder carcinoma cell lines

  摘要：

  2-Arylidenedihydroindole-3-ones were assayed for their antiproliferative and apoptotic abilities as potential drug candidates to treat bladder tumor. These compounds were tested on cell lines obtained from bladder tumors of various stages [superficial (pTa and pT1) vs. invasive (>= pT2)]. The most active compound (3c) inhibited the proliferation, induced apoptosis, and decreased the expression of p-Stat5 and p-Pyk2 in DAG-1 and RT112 lines in which the FGFR3 is either mutated or overexpressed. Knowing that FGFR3 is involved in cell proliferation, differentiation, and migration through cell signaling pathways including p-Stat5 way via p-Pyk2, let us assume that compound 3c may probably act through FGFR3 pathway. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.057

文献信息

• A SHORT METHOD FOR THE SYNTHESIS OF 4,6-DIMETHOXY-1-AZAAURONES
  作者：Martin Ata Lawson、Anne-Marie Mariotte、Ahcene Boumendjel

  DOI：10.1515/hc.2003.9.2.149

  日期：2003.1

  (unsubstituted or monosubstituted on the Α-ring) have been investigated (12). Owing to the important role played by the simultaneous presence of hydroxyl or methoxy groups on 5 and 7 positions, we report herein a simple method for preparation of 4,6-dimethoxyazaaurones. Results and Discussion: Azaaurones were prepared from l-acetyl-4,6-dimethoxy-2,3-dihydro-l//-indole 2 by base-catalyzed condensation with a

  Aurones (Benzylidenebenzofuran-3(2//)-one) 是天然存在的化合物，它是众所周知的黄酮的异构体。与黄酮类化合物一样，环 A 双氧合的 aurone 尤其是在 4 和 6 位上经常在自然界中发现，这种取代模式肯定是对 aurone 生物活性的原因。在本通讯中，我们报告了环 A 氧化的 1氮杂酮的合成。这些分子采用非常接近于 aurone 的构象，并且氮的存在可以允许 SAR 研究的衍生化，并且还可以制备适合分子水溶性的铵盐。4,6-二甲氧基-l-氮杂酮的合成是通过苯甲醛衍生物与l-乙酰基-4,6-二甲氧基-2,3-二氢-l//-吲哚-3酮的缩合来实现的。后者从 3,5-二甲氧基苯胺和氯乙腈开始，分三步制备。如果选择适当的苯甲醛衍生物，该方法可以制备大量氮杂酮。简介 奥隆是属于天然存在的化合物 (1) 中的类黄酮家族的次级代谢物。在植物领域，这些黄酮结构异
• Synthesis and Biological Activities of 1-Azaaurone Derivatives
  作者：Min Zhang、Ting Li、Min Qian、Kailu Li、Yukun Qin、Ting Zhao、Liu-Qing Yang

  DOI：10.1002/jhet.3190

  日期：2018.7

  of 1‐azaaurone derivatives were designed and synthesized from 3,5‐dimethoxyaniline and 2‐chloroacetonitrile. Their structures were characterized by melting point, 1H NMR, IR, and elemental analysis, as well as 13C NMR. The target compounds were evaluated for antitumor activities against human hepatocellular liver carcinoma cell line (HepG‐2) and human cervix carcinoma cell line (Hela) using methyl thiazolyl

  由3,5-二甲氧基苯胺和2-氯乙腈设计并合成了一系列1-氮杂金酮衍生物。它们的结构通过熔点，1 H NMR，IR和元素分析以及13 C NMR表征。使用甲基噻唑基四唑鎓法评估了目标化合物对人肝细胞肝癌细胞系（HepG-2）和人宫颈癌细胞系（Hela）的抗肿瘤活性。结果显示，几种1-氮杂金酮对HepG-2和Hela表现出强大的增殖抑制作用，IC 50范围为5.6–8.8μg/ mL，而不会损害正常细胞。
• Substituted aurone derivatives
  申请人：Phytera, Inc.

  公开号：US06307070B1

  公开（公告）日：2001-10-23

  A method for treating a fungal infection is disclosed. The method includes administering to a patient a pharmaceutical composition containing a compound of formula (IA): where each R is independently H, OH, Br, Cl, I, amino, thiol, nitro, C1-4 alkoxy, C1-4 alkenyloxy, C2-6 alkoxyalkyleneoxy, C1-4 alkylthio, C3-18 alkyl, or C3-18 alkenyl; or two adjacent R's, taken together, are a C2-18 bivalent moiety containing at least one oxgen atom, substituted or disubstituted with A or B or both, A being H, OH, Br, Cl, I, amino, or thiol, and B being H, C1-10 alkyl, C2-18 alkenyl, or C6-18 aryl; provided at least two Rs are not H; X is C4-10 alkyl, C4-20 alkenyl, or a C4-20 single, C6-20 bridged, or C6-20 fused ring moiety containing cycloalkyl, cycloalkenyl, aryl, heterocycle, or heteroaryl, where X is substituted with H, OH, Cl, Br, I, amino, cyano, nitro, alkyl, alkoxy, alkenyl, or alkenyloxy; provided that if X is a heteroaryl or heterocyclic moiety where two Rs are each OH and meta to each other, then the remaining R is H and ortho to each of the two hydroxyls, and Y and Z are each O and a ring atom of X is linked directly to the sp2 carbon atom adjacent to X, then substituted with H, OH, Cl, Br, I, amino, cyano, alkyl, alkoxy, alkenyl, or alkenyloxy; and each of Y and Z is independently selected from O, S, and NH; or a pharmaceutically acceptable salt or ester thereof.

  本发明涉及一种治疗真菌感染的方法，该方法包括向患者施用含有化合物(IA)的药物组合物，其中每个R都是独立的H、OH、Br、Cl、I、氨基、硫醇、硝基、C1-4烷氧基、C1-4烯氧基、C2-6烷氧基烷氧基、C1-4烷基硫基、C3-18烷基或C3-18烯基；或两个相邻的R在一起是一个含有至少一个氧原子的C2-18二价基团，用A或B或两者替代或二者替代，其中A为H、OH、Br、Cl、I、氨基或硫醇，B为H、C1-10烷基、C2-18烯基或C6-18芳基；前提是至少有两个R不是H；X为C4-10烷基、C4-20烯基或含有环烷基、环烯基、芳基、杂环或杂芳基的C4-20单一、C6-20桥式或C6-20融合环基团，其中X被H、OH、Cl、Br、I、氨基、氰基、硝基、烷基、烷氧基、烯基或烯氧基替代；前提是如果X是一个杂芳基或杂环基团，其中两个R分别为OH并且相对于彼此的meta位，那么其余的R为H并且正交于这两个羟基的每一个，而且Y和Z分别为O，并且X的一个环原子直接连接到X相邻的sp2碳原子，然后用H、OH、Cl、Br、I、氨基、氰基、烷基、烷氧基、烯基或烯氧基替代；并且Y和Z中的每一个都是独立选择的O、S和NH；或其药学上可接受的盐或酯。
• 2'-Amino-.ALPHA.-chloroacetophenone as a Valuable Tool for the Synthesis of Conveniently-Substituted .ALPHA.,.BETA.-Epoxychalcone Derivatives
  作者：Madeleine Blanc、Maud Martin、Sabrina Okombi、Ahcène Boumendjel

  DOI：10.1248/cpb.53.435

  日期：——

  The synthesis of conveniently substituted 2′-amino-α,β-epoxychalcones is described. They were obtained through Darzens condensation of 2′-amino-3′,5′-dimethoxy-α-chloroacetophenone with benzaldehydes. The latter can undergo different cyclization possibilities and afford a variety of flavonoid analogs with biological potential.

  本文介绍了方便取代的 2′-氨基-α,β-环氧查耳酮的合成。它们是通过 2′-氨基-3′,5′-二甲氧基-α-氯苯乙酮与苯甲醛的达真缩合而得到的。后者可以发生不同的环化反应，并产生多种具有生物潜力的类黄酮类似物。
• Methods of treating fungal infections
  申请人：——

  公开号：US20020086895A1

  公开（公告）日：2002-07-04

  A method for treating a fungal infection is disclosed. The method includes contacting a fungus with a substituted aurone derivative.

  公开了一种治疗真菌感染的方法。该方法包括将一种取代的黄酮衍生物与真菌接触。