5-nitroferulic acid | 5438-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-nitroferulic acid
• 英文别名: (E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylic acid；(E)-3-(3-nitro-5-methoxy-4-hydroxyphenyl)acrylic acid；(2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylic acid；4-hydroxy-3-methoxy-5-nitro-trans-cinnamic acid；4-Hydroxy-3-methoxy-5-nitro-trans-zimtsaeure；4-Hydroxy-3-methoxy-5-nitrocinnamic acid；3-(4-Hydroxy-3-methoxy-5-nitrophenyl)prop-2-enoic acid；(E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enoic acid
• CAS: 5438-42-6
• 化学式: C₁₀H₉NO₆
• 分子量: 239.185
• InChiKey: PQFQIWNHGCVXIB-NSCUHMNNSA-N

物化性质

• 熔点：
  175 °C(Solv: ethanol (64-17-5))
• 沸点：
  411.2±45.0 °C(Predicted)
• 密度：
  1.501±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-nitroferulic acid 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 (2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-N'-[(1E)-benzylidene]acrylohydrazide
  参考文献：
  名称：

  Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents

  摘要：

  We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d] 11,3)dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazide. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.041
• 作为产物：
  描述：

  阿魏酸 在 硝酸 、 溶剂黄146 作用下， 以65%的产率得到5-nitroferulic acid
  参考文献：
  名称：

  阿魏酸衍生物及其制备方法和应用

  摘要：

  本发明涉及一种本发明涉及阿魏酸衍生物及其制备方法和应用。该阿魏酸衍生物有任一结构式，该阿魏酸衍生物以吉非替尼为阳性对照，结果表明与吉非替尼相比具有良好的活性；为抗肿瘤药物的进一步改造并发现新的抗肿瘤药物候选物具有较高的借鉴与参考价值。本发明还提出了上述阿魏酸衍生物的制备方法及其在制备抗癌药物中的应用。

  公开号：

  CN111808031B

文献信息

• Pharmacologically active compounds, methods for the preparation thereof
  申请人：Orion-yhtyma Oy

  公开号：US04963590A1

  公开（公告）日：1990-10-16

  Pharmacologically active catechol derivatives of formula I ##STR1## wherein R.sub.1 and R.sub.2 independently comprise hydrogen, alkyl, acyl, optionally substituted aroyl, lower alkylsulfonyl or alkylcabamoyl or taken together form a lower alkylidene or cycloalkylidene, X comprises an electronegative substituent such as halogen, nitro, cyano, lower alkylsulfonyl, sulfonamido, aldehyde, caboxyl or trifluoromethyl and R.sub.3 comprises hydrogen, halogen, hydroxy alkyl, amino, nitro, cyano, trifluoromethyl, lower alkylsulfonyl, sulfonamide, aldehyde, alkyl carbonyl, aralkylidene carbonyl or carboxyl or a group selected from ##STR2## wherein R.sub.4 comprises hydrogen, alkyl, cyano, carboxyl or acyl and R.sub.5 comprises hydrogen, cyano, carboxyl, alkoxycarbonyl, carboxyalkenyl, nitro, acyl, optionally substituted aroyl or heteroaroyl, hydroxyalkyl or carboxyalkyl or R.sub.4 and R.sub.5 together form a five to seven membered substituted cycloalkanone ring; --(CO).sub.n (CH.sub.2).sub.m --COR wherein n is 0-1 and m is 0-7 and R comprises hydroxy, alkyl, carboxyalkyl, optionally substituted alkene, alkoxy or optionally substituted amino; ##STR3## wherein R.sub.8 and R.sub.9 independently comprise hydrogen or one of the following optionally substituted groups; alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, or together form an optionally substituted piperidyl group; --NH--CO--R.sub.10 wherein R.sub.10 comprises a substituted alkyl group.

  公式I的药理活性儿茶酚衍生物，其中R.sub.1和R.sub.2独立地包括氢、烷基、酰基、可选择地取代的芳酰基、较低的烷基磺酰基或烷基氨基甲酰基，或者一起形成较低的烷基亚甲基或环烷基亚甲基，X包括电负取代基，如卤素、硝基、氰基、较低的烷基磺酰基、磺胺基、醛基、羧基或三氟甲基，R.sub.3包括氢、卤素、羟基烷基、氨基、硝基、氰基、三
• 2-Aminophenol derivatives
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0081321A1

  公开（公告）日：1983-06-15

  2-AMINOPHENOL derivatives of the general formula: [wherein Z represents a straight alkylene or alkenylene group containing from 1 to 6 carbon atom(s), R1 represents a hydrogen atom, a halogen atom, a straight or branched chain alkyl group containing from 1 to 6 carbon atom(s), a straight or branched chain alkoxy group containing from 1 to 4 carbon atom(s) or a group represented by general formula: (wherein R4 represents a hydrogen atom or a straight or branched chain alkyl group containing from 1 to 6 carbon atom(s).), R2 represents a hydrogen atom, a straight or branched chain alkyl group containing from 1 to 4 carbon atom(s) or a group represented by a formula: R' is attached to the 6th or 4th position of the benzene ring: when R' is attached to the 6th position of the benzene ring, Z-COOR2 is attached to the 4th position of the benzene ring, and when R' is attached to the 4th position of the benzene ring, Z-COOR2 is attached to the 6th position of the benzene ring.] and pharmaceutically acceptable acid addition salts thereof, possess a strong inhibitory effect on 5-lipoxygenase specifically, or 5-lipoxygenase and cyclooxygenase at the same time, and therefore, are useful as treating and preventing agents for diseases which induced by leukotrienes, e.g. allergic tracheal and bronchial diseases or allergic lung diseases, allergic shocks or various allergic inflammations, and various inflammations induced by prostaglandins.

  通式如下的 2-氨基苯酚衍生物： [其中 Z 代表含 1 至 6 个碳原子的直链亚烷基或烯基，R1 代表氢原子、卤素原子、含 1 至 6 个碳原子的直链或支链烷基、含 1 至 4 个碳原子的直链或支链烷氧基或通式如下的基团： (其中 R4 代表氢原子或含有 1 至 6 个碳原子的直链或支链烷基），R2 代表氢原子、含有 1 至 4 个碳原子的直链或支链烷基或由通式表示的基团： R'连接到苯环的第6位或第4位：当R'连接到苯环的第6位时，Z-COOR2连接到苯环的第4位；当R'连接到苯环的第4位时，Z-COOR2连接到苯环的第6位]。 本品及其药学上可接受的酸加成盐对特异性 5-脂氧合酶或同时对 5-脂氧合酶和环氧合酶有很强的抑制作用，因此可作为治疗和预防由白三烯诱发的疾病的药物，如过敏性气管和支气管疾病或过敏性肺部疾病、过敏性休克或各种过敏性炎症以及由前列腺素诱发的各种炎症。
• New use of catechol-o-methyl transferase (comt) inhibitors and their physiologically acceptable salts and esters
  申请人：ORION-YHTYMÄ OY

  公开号：EP0323162A2

  公开（公告）日：1989-07-05

  Catechol derivatives which have been previously suggested for the treatment of Parkinsonism are useful in the treatment and prophylaxis of ulcers and lesions.in the gastrointestinal tract.

  以前曾建议用于治疗帕金森氏症的儿茶酚衍生物可用于治疗和预防胃肠道溃疡和病变。
• Association of snps in the comt locus and neighboring loci with schizophrenia, bipolar disorder, breast cancer and colorectal cancer
  申请人：Darvasi Ariel

  公开号：US20060234223A1

  公开（公告）日：2006-10-19

  Methods and kits used for determining predisposition and/or diagnosis of schizophrenia, bipolar disorder, breast cancer and colorectal cancer using genotypes in the COMT locus are disclosed. Also disclosed are methods and drugs for treating these disorders. Further disclosed are methods and kits useful for prediction drug responsiveness towards mental disorders drugs, and more specifically towards schizophrenia drugs.

  本研究公开了利用 COMT 基因座的基因型确定精神分裂症、双相情感障碍、乳腺癌和结直肠癌的易感性和/或诊断的方法和试剂盒。还公开了治疗这些疾病的方法和药物。还公开了用于预测药物对精神障碍药物，特别是精神分裂症药物的反应性的方法和试剂盒。
• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF MICROBIAL INFECTION(S)<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT D'INFECTION(S) MICROBIENNE(S)
  申请人：UNIV SAINS MALAYSIA

  公开号：WO2016024857A3

  公开（公告）日：2016-10-06