2-Hydroxy-5-methoxy-3-nitro-acetophenon | 90564-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Hydroxy-5-methoxy-3-nitro-acetophenon
• 英文别名: 1-(2-Hydroxy-5-methoxy-3-nitrophenyl)ethanone
• CAS: 90564-25-3
• 化学式: C₉H₉NO₅
• mdl: MFCD17011091
• 分子量: 211.174
• InChiKey: JCPSCOLEARDZDX-UHFFFAOYSA-N

物化性质

• 熔点：
  113–114°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-5-methoxy-3-nitro-acetophenon 在 盐酸 、 tin(II) chloride dihdyrate 、 potassium tert-butylate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.33h， 生成 6-Methoxy-8-[(4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid
  参考文献：
  名称：

  6-Bromo-8-(4-[³H]methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic Acid: A Powerful Tool for Studying Orphan G Protein-Coupled Receptor GPR35

  摘要：

  The potent and selective GPR35 agonist 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (12) was obtained in tritium-labeled form, designated [H-3]PSB-13253, with a specific activity of 36 Ci (1.33 TBq)/mmol. Radiolabeling was achieved by methylation of ethyl 6-bromo-8-(4-((tert-butyldimethylsilyl)oxy)benzamido)-4-oxo-4H-Chromene-2-carboxylate (19) with [H-3]methyl tosylate followed by ester hydrolysis. The radioligand was characterized by kinetic, saturation, and competition assays at membrane preparations of Chinese hamster ovary cells recombinantly expressing the human GPR35. [H-3]12 labeled the receptor with high affinity (K-D = 5.27 nM). Binding was saturable (B-max = 12.6 pmol/mg of protein) and reversible. Affinities of selected standard ligands and a library of amidochromen-4-one-2-carboxylates were determined. Binding data mostly correlated with potencies determined in beta-arrestin assays. On the basis of the test results, several new fluorine-substituted 6-bromo-8-benzamidochromen-4-one-2-carboxylic acids were obtained, which represent the most potent GPR35 agonists known to date. 6-Bromo-8-(2,6-difluoro-4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (83; K-i = 0.589 nM, EC50 = 5.54 nM) showed the highest affinity with a K-i value in the subnanomolar range.

  DOI：

  10.1021/jm4009373
• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 在 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 生成 2-Hydroxy-5-methoxy-3-nitro-acetophenon
  参考文献：
  名称：

  6：8-二羟基黄酮的合成

  摘要：

  描述了合成6：8-二羟基黄酮的途径的工作，其中一种被证明是成功的。

  DOI：

  10.1016/0040-4020(58)88029-1

文献信息

• A synthesis of 6:8-dihydroxyflavone
  作者：J.E. Gown、S.P.MacGiolla Riogh、G.J. MacMahon、S. Ó'Cléirigh、E.M. Philbin、T.S. Wheeler

  DOI：10.1016/0040-4020(58)88029-1

  日期：1958.1

  Work on routes to the synthesis of 6:8-dihydroxyflavone, one of which proved successful, is described.

  描述了合成6：8-二羟基黄酮的途径的工作，其中一种被证明是成功的。
• A Process for Preparing Olodaterol and Intermediates Thereof
  申请人：REDDY G. Pratap

  公开号：US20170260149A1

  公开（公告）日：2017-09-14

  The present invention relates to a process for preparing olodaterol and intermediates thereof. The process comprises of forming compound of Formula 1 by reacting compound of Formula 2 or its acid salt with compound of Formula 3 in the presence of an organic solvent to obtain compound of Formula 4. Protecting groups are removed from compound of Formula 4 in the presence of a suitable solvent to form compound of Formula 1.

  本发明涉及一种制备奥洛达特罗及其中间体的方法。该方法包括通过在有机溶剂存在下，将化合物Formula 2或其酸盐与化合物Formula 3反应形成化合物Formula 1，从而获得化合物Formula 4。在适当溶剂的存在下，从化合物Formula 4中去除保护基，形成化合物Formula 1。
• PROCESS FOR THE MANUFACTURING OF BETAMIMETICS
  申请人：KRUEGER Thomas

  公开号：US20070088160A1

  公开（公告）日：2007-04-19

  The present invention relates to a process for preparing betamimetics of formula 1, wherein n denotes 1 or 2; R 1 denotes hydrogen, halogen, C 1-4 -alkyl or O—C 1-4 -alkyl; R 2 denotes hydrogen, halogen, C 1-4 -alkyl or O—C 1-4 -alkyl; R 3 denotes hydrogen, C 1-4 -alkyl, OH, halogen, O—C 1-4 -alkyl, O—C 1-4 -alkylene-COOH, O—C 1-4 -alkylene-COO—C 1-4 -alkyl.

  本发明涉及一种制备式1的β-受体激动剂的方法，其中n表示1或2；R1表示氢、卤素、C1-4-烷基或O—C1-4-烷基；R2表示氢、卤素、C1-4-烷基或O—C1-4-烷基；R3表示氢、C1-4-烷基、羟基、卤素、O—C1-4-烷基、O—C1-4-亚烷基-羧基、O—C1-4-亚烷基-COO—C1-4-烷基。
• Synthesis and Antitumor Molecular Mechanism of Agents Based on Amino 2-(3′,4′,5′-Trimethoxybenzoyl)benzo[b]furan: Inhibition of Tubulin and Induction of Apoptosis
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Carlota Lopez-Cara、Olga Cruz-Lopez、Maria Dora Carrion、Maria Kimatrai Salvador、Jaime Bermejo、Sara Estévez、Francisco Estévez、Jan Balzarini、Andrea Brancale、Antonio Ricci、Longchuan Chen、Jae Gwan Kim、Ernest Hamel

  DOI：10.1002/cmdc.201100279

  日期：2011.10.4

  compound in this series is 2‐(3′,4′,5′‐trimethoxybenzoyl)‐3‐methyl‐5‐amino‐6‐methoxybenzo[b]furan (3 h), which inhibits cancer cell growth at nanomolar concentrations (IC50=16–24 nM), and interacts strongly with tubulin by binding to the colchicine site. Sub‐G1 apoptotic cells in cultures of HL‐60 and U937 cells were observed by flow cytometric analysis after treatment with 3 h in a concentration‐dependent

  诱导细胞凋亡是一种很有前景的策略，可以导致发现在癌症化疗中具有活性的新分子。当细胞用靶向微管的试剂处理时，通常会观察到这种特性，微管是在细胞分裂中起关键作用的动态结构。苯并[ b ]呋喃等小分子作为微管蛋白聚合的抑制剂很有吸引力。合成并评价了一类基于2-(3',4',5'-三甲氧基苯甲酰基)苯并[ b ]呋喃分子骨架，氨基位于苯环不同位置的新型微管蛋白聚合抑制剂用于抗增殖活性、抑制微管蛋白聚合和细胞周期效应。苯并[ b的苯部分上的甲氧基取代模式]呋喃部分在影响抗增殖活性中起重要作用。在 5-氨基衍生物系列中，如果甲氧基取代基位于 C6 位置，则对细胞生长的抑制作用最大，而 C7 取代基会降低效力。该系列中最有前景的化合物是 2-(3',4',5'-三甲氧基苯甲酰基)-3-甲基-5-氨基-6-甲氧基苯并[ b ]呋喃 ( 3 h )，它以纳摩尔水平抑制癌细胞生长浓度 (IC 50 =16–24
• Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src
  作者：Mark Cushman、Helen Zhu、Robert L. Geahlen、Alan J. Kraker

  DOI：10.1021/jm00046a020

  日期：1994.9

  A series of nitroflavones, 8a-p, and their corresponding aminoflavone hydrochloride salts, 10a-p, was synthesized. The preparation of nitroflavones 8b-i,o,p began with commercially available o-hydroxyacetophenones 2b-f which were converted to o-hydroxynitroacetophenones 3a-h via a variety of nitration methods, followed by condensation with nitrobenzoyl chlorides and cyclization under acidic condition. The nitroflavones 8aj-n were prepared by nitration of the corresponding flavones 7a-e. These new compounds were evaluated for their abilities to inhibit the in. vitro protein-tyrosine kinase activities of p56(1ck), EGFr, and p60(v-src), and all of the active compounds were amino-substituted flavones. None of the nitroflavones inhibited the enzymes. The most active substance in this series against p56(lck) was compound 10j, which had an IC50 of is mu M. When tested versus EGFr, compounds 10a,m displayed IC50's of 8.7 and 7.8 mu M, respectively. Against p60(v-src), 10a,m showed IC50 values of 28.8 and 38.4 mu M, respectively.