2,3,4-trimethoxy-6-nitrobenzoic acid | 61948-84-3

• 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: 2,3,4-trimethoxy-6-nitrobenzoic acid
• CAS: 61948-84-3
• 化学式: C₁₀H₁₁NO₇
• 分子量: 257.2
• InChiKey: DSONWCVMECGSKN-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  428.8±45.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxy-6-nitrobenzoic acid 在 palladium on activated charcoal 哌啶 、 氢气 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲醇 、 1,2-二氯乙烷 、 异丙醇 为溶剂， 反应 22.0h， 生成 (3-Bromo-phenyl)-(5,6,7-trimethoxy-quinazolin-4-yl)-amine
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 8. An Unusually Steep Structure−Activity Relationship for Analogues of 4-(3-Bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a Potent Inhibitor of the Epidermal Growth Factor Receptor

  摘要：

  4-(3-Bromoanilino)-6,7-dimethoxyquinazoline (32, PD 153035) is a very potent inhibitor (IC50 0.025 nM) of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR), binding competitively at the ATP site. Structure-activity relationships for close analogues of 32 are very steep. Some derivatives have IC(50)s UP to 80-fold better than predicted from simple additive binding energy arguments, yet analogues possessing combinations of similar phenyl and quinazoline substituents do not show this ''supra-additive'' effect. Because some substituents which are mildly deactivating by themselves can be strongly activating when used in the correct combinations, it is proposed that certain substituted analogues possess the ability to induce a change in the conformation of the receptor when they bind. There is some bulk tolerance for substitution in the 6- and 7-positions of the quinazoline, so that 32 is not the optimal inhibitor for the induced conformation. The diethoxy derivative 56 [4-(3-bromoanilino)-6,7-diethoxyquinazoline] shows an IC50 Of 0.006 nM, making it the most potent inhibitor of the tyrosine kinase activity of the EGFR yet reported.

  DOI：

  10.1021/jm9503613
• 作为产物：
  描述：

  methyl 2,3,4-trimethoxy-6-nitrobenzoate 在 氢氧化钾 作用下， 生成 2,3,4-trimethoxy-6-nitrobenzoic acid
  参考文献：
  名称：

  Pollak; Goldstein, Justus Liebigs Annalen der Chemie, 1907, vol. 351, p. 168

  摘要：

  DOI：

文献信息

• [EN] FUSED-RING PYRIMIDIN-4(3H)-ONE DERIVATIVES, PROCESSES FOR THE PREPARATION AND USES THEREOF<br/>[FR] DERIVES DE LA PYRIMIDIN-4(3H)-ONE A CYCLES FUSIONNES, SPN PROCEDE DE PREPARATION ET SES UTILISATIONS
  申请人：SANKYO CO

  公开号：WO2003106435A1

  公开（公告）日：2003-12-24

  AbstractNovel compounds of the following formula (I) and pharmacologically acceptable salt and esters thereof can modulate LXR function and as a result show excellent anti-arteriosclerotic and anti-inflammatory activity:wherein:A represents aryl or heteroaryl;R1, R2 and R3 are the same or different and each represents hydrogen, hydroxyl, nitro, cyano, amino, halogen, carboxy, carbamoyl, mercapto, alkyl, haloalkyl, alkylcarbonyloxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, N-(alkylcarbonyl)-N-(alkyl)amino, alkoxycarbonylamino, N-(alkoxycarbonyl)-N-(alkyl)amino, alkylsulfonylamino, N-(alkylsulfonyl)-N-(alkyl)amino, haloalkylsulfonylamino, N-(haloalkylsulfonyl)-N-(alkyl)amino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, or R1 and R2 together are alkylenedioxy;R4 and R5 are the same or different and each represents hydrogen, hydroxyl, amino, halogen, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl or alkylthio;X represents hydrogen, hydroxyl, halogen, alkoxy or haloalkoxy; andY represents an optionally substituted alkyl, cycloalkyl, heterocyclyl, aryl, cycloalkylalkyl, heterocyclylalkyl or aralkyl group.

  新化合物具有以下式（I）的结构，其药学上可接受的盐和酯可以调节LXR功能，从而表现出优秀的抗动脉粥样硬化和抗炎活性：其中：A代表芳基或杂环芳基；R1、R2和R3相同或不同，每个代表氢、羟基、硝基、氰基、氨基、卤素、羧基、氨基甲酰基、巯基、烷基、卤代烷基、烷基羰氧基、烷氧基、烷硫基、烷磺基、烷基氨基、二烷基氨基、烷基羰基氨基、N-（烷基羰基）-N-（烷基）氨基、烷氧羰基氨基、N-（烷氧羰基）-N-（烷基）氨基、烷磺酰氨基、N-（烷磺酰基）-N-（烷基）氨基、卤代烷基磺酰氨基、N-（卤代烷基磺酰基）-N-（烷基）氨基、烷基羰基、烷氧羰基、烷基氨基羰基或二烷基氨基羰基，或R1和R2一起是亚烷二氧基；R4和R5相同或不同，每个代表氢、羟基、氨基、卤素、巯基、烷基、卤代烷基、烷氧基、烷氧羰基或烷硫基；X代表氢、羟基、卤素、烷氧基或卤代烷氧基；Y代表可选择取代的烷基、环烷基、杂环烷基、芳基、环烷基烷基、杂环烷基烷基或芳基烷基。
• Synthesis and anticancer activities of 4-(4-substituted piperazin)-5,6,7-trialkoxy quinazoline derivatives
  作者：Ying Zhang、Yin-Jiu Huang、Hong-Mei Xiang、Pei-Yi Wang、De-Yu Hu、Wei Xue、Bao-An Song、Song Yang

  DOI：10.1016/j.ejmech.2014.03.036

  日期：2014.5

  A series of 4-(4-substituted piperazin)-5,6,7-trialkoxy quinazoline was prepared by conventional heating methods. Among these compounds, the crystal structure of compound 10o (CCDC: 916922) was determined by X-ray crystallography. Bioassay results showed that most target compounds had certain inhibition activities against proliferation of tumor cells, and some compounds even had good broad-spectrum

  通过常规加热方法制备了一系列4-（4-取代的哌嗪）-5,6,7-三烷氧基喹唑啉。在这些化合物中，化合物10o（CCDC：916922）的晶体结构通过X射线晶体学测定。生物测定结果表明，大多数目标化合物对肿瘤细胞的增殖具有一定的抑制活性，有些化合物甚至具有良好的广谱抑制活性。乙氧基系列化合物比甲氧基系列化合物对肿瘤细胞具有更高的抑制活性。生物活性测试表明，化合物10s的IC 50值相对于PC3，MGC803，A375和A549细胞分别为1.8、2.8、1.3和2.9μM，远高于商品吉非替尼（分别为7.2、7.6、7.2和9.8μM）。相反，化合物10s对NH3T3的IC 50值非常低，表明对正常细胞的作用很小，这也可以通过乳酸脱氢酶和a啶橙/溴化乙锭染色来证明。细胞构型和细胞周期的分析表明，化合物10s可能通过抑制24 h的细胞增殖而使细胞停留在G 0 / G 1相。复合10s也抑制ERK1
• Pyrrolbenzodiazepines
  申请人：Spirogen Limited

  公开号：US07049311B1

  公开（公告）日：2006-05-23

  Compounds of formula (Ia) and (Ib) wherein A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula (Ia) or (Ib), where the R8 groups of the monomers form together a bridge having the formula —X—R′—X— linking the monomers, where R′ is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon—carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula (Ia) when A is a single bond, then R2 is not CH═CH(CONH2) or CH═CH(CONMe2). Other related compounds are also disclosed

  化合物的公式(Ia)和(Ib)，其中A为CH2或单键；R2从以下选取：R、OH、OR、CO2H、CO2R、COH、COR、SO2R、CN；R6、R7和R9独立地从H、R、OH、OR、卤素、氨基、NHR、硝基、Me3Sn中选取；R8从H、R、OH、OR、卤素、氨基、NHR、硝基、Me3Sn中选取，其中R如上所定义，或该化合物是二聚体，每个单体都是公式(Ia)或(Ib)的相同或不同，其中单体的R8基共同形成一个桥，该桥具有公式—X—R′—X—，连接单体，其中R′是含有3到12个碳原子的烷基链，该链可以被一个或多个杂原子和/或芳香环打断，并且可以包含一个或多个碳-碳双键或三键，每个X独立地从O、S或N中选取；但在公式(Ia)的化合物中，当A为单键时，R2不是CH═CH(CONH2)或CH═CH(CONMe2)。还披露了其他相关化合物。
• 喹唑啉酮类化合物或其可药用的盐、异构体及其制备方法、药物组合物和用途
  申请人：中国药科大学

  公开号：CN113754594A

  公开（公告）日：2021-12-07

  本发明公开了具有通式I所示结构的喹唑啉酮类化合物或其可药用的盐、异构体及其制备方法、药物组合物和用途，本发明克服了现有广谱抗病毒药物结构单一、非共价类高效小分子抑制剂缺乏等缺陷，对3C样半胱氨酸蛋白酶具有很好的抑制活性，对病毒感染性疾病具有良好的治疗作用，毒副作用较小。
• 2-(1-Piperazinyl)-4-pyrimidinamines and related compounds
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0039190A1

  公开（公告）日：1981-11-04

  The invention concerns a compound of formula I in which R1 and R2 are hydrogen, or R1 and R2 together form a chain of the formula wherein R6, R7, R8 and R9 each is hydrogen or lower alkoxy; R3 is one of the following or wherein R10 is hydrogen or at least one substituent selected from halo, lower alkyl, lower alkoxy, hydroxy, 1-oxo (lower) alkoxy or NR"R12 wherein R" and R12 each is hydrogen or lower alkyl; A is 0, S or NR13 wherein R13 is hydrogen or lower alkyl; R4 and R5 each is hydrogen or lower alkyl; and n is 1 or 2; or a therapeutically acceptable acid addition salt thereof, the term "lower alkyl" as used herein means straight chain alkyl radicals containing from 1 to 6 carbon atoms and branched chain alkyl radicals containing from 3 to 4 carbon atoms, the term "lower alkoxy" as used herein means straight chain alkoxy radicals containing from 1 to 6 carbon atoms and branched chain alkoxy radicals containing 3 to4 carbon atoms and the term "1-oxo(lower)alkoxy" as used herein means straight chain 1-oxoalkoxy radicals containing from 2 to 6 carbon atoms and branched chain 1-oxoalkoxy radicals containing 4 to 6 carbon atoms. Processesforthe preparation of compounds of formula I and their use in pharmaceutical compositions and for the treatment of hypertension are also described.

  本发明涉及一种式 I 的化合物 其中 R1 和 R2 为氢，或 R1 和 R2 共同形成一条式链 其中 R6、R7、R8 和 R9 各为氢或低级烷氧基； R3 为下列之一 或 其中 R10 是氢或至少一个选自卤代、低级烷基、低级烷氧基、羟基、1-氧代（低级）烷氧基或 NR "R12 的取代基，其中 R" 和 R12 各自是氢或低级烷基；A 是 0、S 或 NR13，其中 R13 是氢或低级烷基；R4 和 R5 各自是氢或低级烷基；n 是 1 或 2；或其治疗上可接受的酸加成盐，本文所用术语 "低级烷基 "是指含有 1 至 6 个碳原子的直链烷基和含有 3 至 4 个碳原子的支链烷基、本文所用术语 "低级烷氧基 "是指含有 1 至 6 个碳原子的直链烷氧基和含有 3 至 4 个碳原子的支链烷氧基，本文所用术语 "1-氧代（低级）烷氧基 "是指含有 2 至 6 个碳原子的直链 1-氧代烷氧基和含有 4 至 6 个碳原子的支链 1-氧代烷氧基。 还描述了式 I 化合物的制备过程及其在药物组合物和治疗高血压中的用途。