2-amino-5-(N,N-dimethylamino)acetophenone | 98440-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-5-(N,N-dimethylamino)acetophenone
• 英文别名: 2-amino-5-(dimethylamino)acetophenone；5-(dimethylamino)-2-aminoacetophenone；1-(2-amino-5-dimethylamino-phenyl)-ethanone；1-(2-Amino-5-dimethylamino-phenyl)-aethanon；2-Amino-5-dimethylamino-acetophenon；1-[2-Amino-5-(dimethylamino)phenyl]ethanone
• CAS: 98440-66-5
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: KYSZYGWHDKZFKY-UHFFFAOYSA-N

物化性质

• 熔点：
  68-71 °C
• 沸点：
  332.3±27.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-(N,N-dimethylamino)acetophenone 在 碘 、 magnesium 、 三乙胺 、 三甲氧基磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.17h， 生成
  参考文献：
  名称：

  N-烷基-N-（2-（1-（芳基乙烯基）芳基）肉桂酰胺的光催化分子内[2 + 2]环加成反应

  摘要：

  N-烷基-N-（ 2-（1-芳基乙烯基）芳基）肉桂酰胺通过铱光催化的分子内[2 + 2]光环加成反应转变为天然产物。该协议具有广泛的底物范围，同时在温和的反应条件下运行。束缚形成三取代的环丁烷核心的四个成分会迅速建立高分子复杂性。我们的方法允许设计和合成多种四氢环丁酮[ c ]喹啉-3（1 H）-酮，产率在20–99％之间，并且具有出色的区域选择性和非对映选择性。此外，已证明在环丁烷环断裂后，1,7-烯炔的分子内[2 + 2]-环加成反应会导致类似烯炔的复分解。

  DOI：

  10.1002/chem.202003641
• 作为产物：
  描述：

  3-氯苯乙酮 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 作用下， 生成 2-amino-5-(N,N-dimethylamino)acetophenone
  参考文献：
  名称：

  Antitumor Agents 155. Synthesis and Biological Evaluation of 3',6,7-Substituted 2-Phenyl-4-quinolones as Antimicrotubule Agents

  摘要：

  A series of 3',6,7-substituted 2-phenyl-4-quinolones were designed and synthesized as antimitotic antitumor agents. All compounds showed cytotoxic effects (log GI(50) less than or equal to -4.0; log drug molar concentration required to cause 50% inhibition) against the growth of a variety of human tumor cell lines, including those derived from solid tumors such as non-small cell lung, colon, central nervous system, ovary, prostate, and breast cancers, when evaluated in the National Cancer Institute's 60 human tumor cell line in vitro screen. The most potent compound (26) demonstrated strong cytotoxic effects with GI(50) values in the nanomolar or subnanomolar range in almost all the tumor cell lines. Compound 26 was also a potent inhibitor of tubulin polymerization and radiolabeled colchicine binding to tubulin, with activity comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4.

  DOI：

  10.1021/jm00046a025

文献信息

• Synthesis and cardiotonic activity of a series of substituted 4-alkyl-2(1H)-quinazolinones
  作者：Victor T. Bandurco、Charles F. Schwender、Stanley C. Bell、Donald W. Combs、Ramesh M. Kanojia、Seymour D. Levine、Dennis M. Mulvey、Mary A. Appollina、Marianne S. Reed

  DOI：10.1021/jm00391a026

  日期：1987.8

  The synthesis, cardiac fraction III cyclic nucleotide phosphodiesterase (PDE-III) inhibition, and positive inotropic activity of a series of 2(1H)-quinazolinones are reported. A general synthesis of the series involved the cyclization of 2-aminoacetophenones with potassium cyanate in acetic acid. Modifications at the 4-position of the quinazoline nucleus were best achieved by formation of the intermediate

  报告了一系列2（1H）-喹唑啉酮的合成，心脏分数III环状核苷酸磷酸二酯酶（PDE-III）抑制和正性肌力活性。该系列的一般合成涉及2-氨基苯乙酮与氰酸钾在乙酸中的环化。通过由取代的异氰酸苯酯和适当的羧酰胺形成中间体N1-酰基-N3-苯基脲，可以最佳地实现喹唑啉核4位的修饰。PPA用于接近喹唑啉产物。通常，该系列的SAR与先前针对PDE-III抑制而发表的五点模型相似。该系列中活性最高的类似物是5,6-二甲氧基-4-甲基-2（1H）-喹唑啉酮（1）（ORF 16600），其氨力农的静脉内效力约为其两倍。
• SYNTHESIS AND ANTICANCER ACTIVITY OF ARYL AND HETEROARYL-QUINOLIN DERIVATIVES
  申请人：Kuo Sheng-Chu

  公开号：US20120015908A1

  公开（公告）日：2012-01-19

  A compound of Formula I is disclosed as follows: or a pharmaceutically acceptable salt, prodrug, solvate, or metabolite thereof, wherein R is hydrogen, P(═O)(OH) 2 , P(═O)(O(C 1 -C 18 )alkylene(C 6 -C 20 )aryl) 2 , P(═O)(OH)(OM), P(═O)(OM) 2 , P═O(O 2 M), S(═O)(OH) 2 , S(═O)(O(C 1 -C 18 )alkylene(C 6 -C 20 )aryl) 2 , S(═O)(OH)(OM), S(═O)(OM) 2 ; M is a monovalent or divalent metal ion, or alkylammonium ion; W is (C 6 -C 20 )aryl, (C 6 -C 20 )heteroaryl, (C 1 -C 18 )alkyl(C 6 -C 20 )aryl, (C 1 -C 18 )alkyl(C 6 -C 20 )heteroaryl, hydroxy(C 6 -C 20 )aryl, hydroxy(C 6 -C 20 )heteroaryl, (C 1 -C 18 )alkoxy(C 6 -C 20 )aryl, (C 1 -C 18 )alkoxy(C 6 -C 20 )heteroaryl, (C 1 -C 18 )alkylenedioxy(C 6 -C 20 )aryl, (C 1 -C 18 )alkylenedioxy(C 6 -C 20 )heteroaryl, halo(C 6 -C 20 )aryl, halo(C 6 -C 20 )heteroaryl, (C 1 -C 18 )alkylamino(C 6 -C 20 )aryl, (C 1 -C 18 )alkylamino(C 6 -C 20 )heteroaryl, (C 1 -C 18 )cycloalkylamino(C 6 -C 20 )aryl, or (C 1 -C 18 )cycloalkylamino(C 6 -C 20 )heteroaryl, and their OR 8 substutes; R 5 is (C 1 -C 18 alkoxy, hydrogen, hydroxyl, O—(C 1 -C 18 )alkyl(C 6 -C 20 )aryl, halo or OR 8 , or R 5 and R 6 are (C 1 -C 18 )dioxy provided that R 7 is hydrogen; R 6 is hydroxyl, O—(C 1 -C 18 )alkyl(C 6 -C 20 )aryl, halo or OR R , (C 1 -C 18 )alkoxy, (C 1 -C 18 )alkylamino, or (C 1 -C 18 )cycloalkylamino, or R 6 and R 7 are (C 1 -C 18 )dioxy provided that R 5 is hydrogen; R 7 is hydrogen, halo or OR 8 , hydroxyl, or O—(C 1 -C 18 )alkyl(C 6 -C 20 )aryl; and R 8 is P(═O)(OH) 2 , P(═O)(O(C 1 -C 18 )alkyl(C 6 -C 20 )aryl) 2 , P(═O)(OH)(OM), or P(═O)(OM) 2 , P═O(O 2 M).

  根据以下公式披露了一种化合物：或其药学上可接受的盐、前药、溶剂合物或代谢物，其中R为氢、P(═O)(OH)2、P(═O)(O(C1-C18)烷基(C6-C20)芳基)2、P(═O)(OH)(OM)、P(═O)(OM)2、P═O(O2M)、S(═O)(OH)2、S(═O)(O(C1-C18)烷基(C6-C20)芳基)2、S(═O)(OH)(OM)、S(═O)(OM)2；M为一价或二价金属离子，或烷基铵离子；W为(C6-C20)芳基、(C6-C20)杂芳基、(C1-C18)烷基(C6-C20)芳基、(C1-C18)烷基(C6-C20)杂芳基、羟基(C6-C20)芳基、羟基(C6-C20)杂芳基、(C1-C18)烷氧基(C6-C20)芳基、(C1-C18)烷氧基(C6-C20)杂芳基、(C1-C18)烷二氧基(C6-C20)芳基、(C1-C18)烷二氧基(C6-C20)杂芳基、卤代(C6-C20)芳基、卤代(C6-C20)杂芳基、(C1-C18)烷基氨基(C6-C20)芳基、(C1-C18)烷基氨基(C6-C20)杂芳基、(C1-C18)环烷基氨基(C6-C20)芳基，或(C1-C18)环烷基氨基(C6-C20)杂芳基，以及它们的OR8取代基；R5为(C1-C18)烷氧基、氢、羟基、O—(C1-C18)烷基(C6-C20)芳基、卤素或OR8，或R5和R6为(C1-C18)二氧基，前提是R7为氢；R6为羟基、O—(C1-C18)烷基(C6-C20)芳基、卤素或ORR、(C1-C18)烷氧基、(C1-C18)烷基氨基，或(C1-C18)环烷基氨基，或R6和R7为(C1-C18)二氧基，前提是R5为氢；R7为氢、卤素或OR8、羟基，或O—(C1-C18)烷基(C6-C20)芳基；R8为P(═O)(OH)2、P(═O)(O(C1-C18)烷基(C6-C20)芳基)2、P(═O)(OH)(OM)、或P(═O)(OM)2、P═O(O2M)。
• [EN] SYNTHESIS AND ANTICANCER ACTIVITY OF ARYL AND HETEROARYL-QUINOLIN DERIVATIVES<br/>[FR] SYNTHÈSE ET ACTIVITÉ ANTICANCÉREUSE DE DÉRIVÉS D'ARYL- ET D'HÉTÉROARYL-QUINOLÉINE
  申请人：EFFICIENT PHARMA MAN CORP

  公开号：WO2012009519A1

  公开（公告）日：2012-01-19

  A class of compounds that are derivatives and analogues of aryl and heteroaryl-quinolin is disclosed. Also disclosed are synthesis and use of the aryl and heteroaryl -quinolin derivatives and analogues for anticancer activities.

  本文披露了一类衍生自芳基和杂环芳基喹啉的化合物及其类似物。本文还披露了合成和使用这些芳基和杂环芳基喹啉衍生物和类似物进行抗癌活性的方法。
• Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0138491A2

  公开（公告）日：1985-04-24

  The synthesis of substituted 2(1H)-quinazolinone-1-alkanoic acids and their esters is described. The novel quinazolinones are renal vasodilators and as such reduce vascular resistance to renal blood flow. The quinazolinones are useful as cardiovascular agents.

  介绍了取代的 2(1H)-喹唑啉酮-1-烷酸及其酯类的合成。 新型喹唑啉酮类是肾血管扩张剂，因此可降低肾血流的血管阻力。 喹唑啉酮类可用作心血管药物。
• Method of improving sleep
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0285219A2

  公开（公告）日：1988-10-05

  The use for the manufacture of a medicament for improving sleep and treating sleep disorders of a piperazine derivative of formula wherein R1 is hydrogen or C, alkyl; X is C16 alkyl, hydroxyC, 6 alkyl, C, alkyloxyC16 alkyl, aminocarbonyl, mono-and di(C16 alkyl)-aminocarbonyl, carboxyl, C, alkyloxycarbonyl, (aminocarbonyl)C16 alkyl, [mono-and di(C, alkyl)-aminocarbonyl]C16 alkyl, carboxylC, 6 alkyl, (C, 6 alkyloxycarbonyl)C, alkyl or (hydroxyC16alkyl)-aminocarbonyl; R2 is hydrogen or C, 6 alkyl; Ar is phenyl, pyridinyl, pyrazolyl, all three being optionally substituted, or a radical of formula Q is aryl, aryloxy, diarylmethoxy, 2,2-diarylethenyl, diarylmethylcarbonyl, arylcarbonyl, mono-and diarylaminocarbonyl, diarylmethyl or arylamino, the amino moiety in said arylamino being optionally substituted, the pharmaceutically acceptable acid addition salts and possible stereochemically isomeric forms thereof; novel compounds of formula (I); pharmaceutical compositions containing the latter compounds as an active ingredient and methods of preparing said compounds and pharmaceutical compositions.

  式中的哌嗪衍生物用于制造改善睡眠和治疗睡眠障碍的药物 其中R1为氢或C, 烷基； X是C16烷基、羟基C，6烷基、C，6烷氧基C16烷基、氨基羰基、单和二(C16烷基)-氨基羰基、羧基、C，6烷氧基羰基、(氨基羰基)C16烷基、[单和二(C，烷基)-氨基羰基]C16烷基、羧基C，6烷基、(C，6烷氧基羰基)C，烷基或(羟基C16烷基)-氨基羰基； R2 是氢或 C, 6 烷基； Ar 是苯基、吡啶基、吡唑基（三者均可选择被取代）或式中的一个基团 Q 是芳基、芳氧基、二芳甲氧基、2,2-二芳基乙烯基、二芳甲基羰基、芳基羰基、单芳基和二芳基氨基羰基、二芳甲基或芳基氨基，所述芳基氨基中的氨基被任选取代；药学上可接受的酸加成盐及其可能的立体化学异构形式；式 (I) 的新型化合物；含有后一种化合物作为活性成分的药物组合物以及制备所述化合物和药物组合物的方法。