3-氯-5-羟基-4-甲氧基苯甲醛 | 54246-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-氯-5-羟基-4-甲氧基苯甲醛
• 英文名称: 3-chloro-5-hydroxy-4-methoxybenzaldehyde
• 英文别名: 3-Chlor-5-hydroxy-4-methoxy-benzaldehyd；3-Chlor-5-hydroxy-4-methoxybenzaldehyd
• CAS: 54246-06-9
• 化学式: C₈H₇ClO₃
• 分子量: 186.595
• InChiKey: OGAFORQFPLHRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  3-氯-5-羟基-4-甲氧基苯甲醛 在 吡啶 、 aluminum (III) chloride 作用下， 以 氯仿 为溶剂， 生成 3-氯-4,5-二羟基苯甲醛
  参考文献：
  名称：

  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives

  摘要：

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.024
• 作为产物：
  描述：

  5-甲酰基-2-甲氧基苯基 乙酸酯 在 1,4-二氯哌嗪 、 sodium hydroxide 作用下， 以 硫酸 为溶剂， 反应 3.0h， 生成 3-氯-5-羟基-4-甲氧基苯甲醛
  参考文献：
  名称：

  Syntheses of Chlorinated Bisbibenzyls from Bryophytes

  摘要：

  在检测到的不同苔藓植物中的异型二苯并双芴类的氯化物，是通过一种高效的、灵活的单元构建系统合成的，该系统广泛采用了铃木和维蒂希方案。

  DOI：

  10.1055/s-2002-35629

文献信息

• Catechol O-methyltransferase. 10. 5-Substituted, 3-hydroxy-4-methoxybenzoic acids (isovanillic acids) and 5-substituted, 3-hydroxy-4-methoxybenzaldehydes (isovanillins) as potential inhibitors
  作者：Ronald T. Borchardt、Joan H. Huber、Michael Houston

  DOI：10.1021/jm00345a012

  日期：1982.3

  and evaluated as inhibitors of rat liver catechol O-methyltransferase. The compounds exhibited either noncompetitive or competitive patterns of inhibition when 3,4-dihydroxybenzoic acid was the variable substrate. The benzaldehydes were significantly more potent inhibitors than the corresponding benzoic acids, and electron-withdrawing substituents in the 5 position greatly enhanced their inhibitory

  已经合成了一系列5-取代的3-羟基-4-甲氧基苯甲酸（异香草酸）和-苯甲醛（异香草醛），并将其作为大鼠肝儿茶酚O-甲基转移酶的抑制剂。当3,4-二羟基苯甲酸是可变底物时，化合物表现出非竞争性或竞争性抑制作用。苯甲醛是比相应的苯甲酸明显更有效的抑制剂，并且5位的吸电子取代基大大提高了它们的抑制活性。
• MORPHOLINE DERIVATIVE
  申请人：Akatsuka Hidenori

  公开号：US20100240644A1

  公开（公告）日：2010-09-23

  The present invention provides a morpholine derivative of the formula [I]; wherein R 1 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, a cycloalkyl group or an alkyl group; R 2 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted heterocyclo-substituted carbonyl group or a cycloalkylcarbonyl group; T is a methylene group or a carbonyl group; R 3 , R 4 , R 5 and R 6 are the same or different and a hydrogen atom, an optionally substituted carbamoyl group or an optionally substituted alkyl group; or pharmaceutically acceptable salts thereof. These compounds are useful as a renin inhibitor.

  本发明提供了公式[I]的吗啡啶衍生物；其中R1是取代的烷基，可选取代的芳基，可选取代的杂环基，环烷基或烷基；R2是取代的烷基，可选取代的芳基，可选取代的杂环基，可选取代的烷基羰基，可选取代的芳基羰基，可选取代的杂环取代羰基或环烷基羰基；T是亚甲基或羰基；R3，R4，R5和R6相同或不同，是氢原子，可选取代的氨基甲酰基或可选取代的烷基；或其药学上可接受的盐。这些化合物可用作肾素抑制剂。
• STILBENE COMPOUNDS FOR USE IN THE TREATMENT OF TUMOUR AND EYE DISEASES
  申请人：Guangzhou AnHao Pharmaceutical Technology Co., Ltd.

  公开号：EP4342463A1

  公开（公告）日：2024-03-27

  Provided is the use of stilbene compounds in the preparation of anti-tumor medicaments, and related is the pharmaceutical field. The stilbene compounds of the present invention are compounds represented by formula I, or salts thereof, or stereoisomers thereof, or solvates thereof. In the present invention, it is discovered that stilbene compounds have a dual effect of enriching T lymphocytes CD8+ in solid tumors and targeting the destruction of the inner wall of tumor blood vessels. While killing tumor cells by cytotoxic T lymphocyte antigen CD8+, the stilbenes cut off the blood supply to tumor tissues, cause rapid necrosis in solid tumors, greatly improve the killing effects on tumors, and inhibit tumor metastasis. Thereby, they can be used to prepare anti-tumor medicaments, and also used in combination with tumor immunotherapeutics to achieve synergistic anti-tumor effects. In addition, the stilbene compounds of the present invention can inhibit the growth of ocular surface blood vessels and be used in the preparation of medicaments for treating various eye diseases. The stilbene compounds of the present invention have good application prospects.

  提供的一种用途是茋类化合物在制备抗肿瘤药物中的应用，及其相关的药代动力学领域。本发明的茋类化合物是由式(I)所表示的化合物，或者其盐，或者其立体异构体，或者其溶剂化合物。在本发明中发现芪类化合物对于固体瘤内具有双重作用，一方面使得T淋巴细胞CD8+在实体瘤内富集，另一方面对于肿瘤血管内皮具有靶向性的破坏作用。芪类化合物在通过细胞毒性T淋巴细胞抗原CD8+杀死肿瘤细胞的同时，切断肿瘤组织的血液供应，使实体瘤快速坏死，大大提高了对肿瘤的杀伤效果，抑制肿瘤转移，从而可以制备成抗肿瘤药物，也可以与肿瘤免疫治疗药物联合使用达到协同抗肿瘤的效果。此外，本发明的芪类化合物还可以抑制眼表血管增生，具有制备治疗各类眼科疾病的药物的用途。本发明的芪类化合物具有良好的应用前景。
• MORPHOLINE DERIVATIVES AS RENIN INHIBITORS
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2168952B1

  公开（公告）日：2017-02-15
• BORCHARDT, R. T.;HUBER, J. A.;HOUSTON, M., J. MED. CHEM., 1982, 25, N 3, 258-263
  作者：BORCHARDT, R. T.、HUBER, J. A.、HOUSTON, M.

  DOI：——

  日期：——