3-溴-5-羟基-4-甲氧基苯甲酸 | 52783-66-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-5-羟基-4-甲氧基苯甲酸
• 英文名称: 3-bromo-5-hydroxy-4-methoxybenzoic acid
• 英文别名: 5-Brom-isovanillinsaeure
• CAS: 52783-66-1
• 化学式: C₈H₇BrO₄
• 分子量: 247.045
• InChiKey: XKPMZMJYQDNWDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-溴-5-羟基-4-甲氧基苯甲醛	5-Brom-isovanillin	23354-30-5	C8H7BrO3	231.046
  5-溴-3, 4-二羟苯甲醛	3-bromo-4,5-dihydroxybenzaldehyde	16414-34-9	C7H5BrO3	217.019

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3-羟基-4-甲氧基苯甲酸	Isovanillic acid	645-08-9	C8H8O4	168.149

反应信息

• 作为反应物：
  描述：

  3-溴-5-羟基-4-甲氧基苯甲酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 生成 3-羟基-4-甲氧基苯甲酸
  参考文献：
  名称：

  Brominated phenylalanines

  摘要：

  Abstract(3‐(3‐Bromo‐4‐hydroxy‐S‐methoxy‐phenyl)alanine (Ie) exerts a long‐acting antihypertensive effect in rats and dogs : its synthesis and its optical resolution have already appeared in the literature. 1 Ten new mono‐ and polybrominated phenylalanines with hydroxy‐ and/or methoxy‐groups are here described. These unnatural amino‐acide were synthesized by direct bromination, or via the acetamidomalonic esters (V), or via the azlactones (VI) and the corresponding phenylpyruvic acids (VIII).

  DOI：

  10.1002/bscb.19740830304
• 作为产物：
  描述：

  2-氯-N-(4-氯苯基)-5-硝基苯甲酰胺 在 sodium hydroxide 、 silver nitrate 作用下， 反应 0.25h， 以43%的产率得到3-溴-5-羟基-4-甲氧基苯甲酸
  参考文献：
  名称：

  邻苯二酚O-甲基转移酶。10.作为潜在抑制剂的5-取代的3-羟基-4-甲氧基苯甲酸（异香草醛酸）和5-取代的3-羟基-4-甲氧基苯甲醛（异香草醛）。

  摘要：

  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。

  DOI：

  10.1021/jm00345a012

文献信息

• Discovery of a Potent and Selective Fragment-like Inhibitor of Methyllysine Reader Protein Spindlin 1 (SPIN1)
  作者：Yan Xiong、Holger Greschik、Catrine Johansson、Ludwig Seifert、Johannes Bacher、Kwang-su Park、Nicolas Babault、Michael Martini、Vincent Fagan、Fengling Li、Irene Chau、Thomas Christott、David Dilworth、Dalia Barsyte-Lovejoy、Masoud Vedadi、Cheryl H. Arrowsmith、Paul Brennan、Oleg Fedorov、Manfred Jung、Gillian Farnie、Jing Liu、Udo Oppermann、Roland Schüle、Jian Jin

  DOI：10.1021/acs.jmedchem.9b00522

  日期：2019.10.24

  compound library, we identified that UNC0638, a highly potent inhibitor of the histone methyltransferases G9a and GLP, was a weak inhibitor of SPIN1 (spindlin 1), a methyllysine reader protein. Our optimization of this weak hit resulted in the discovery of a potent, selective, and cell-active SPIN1 inhibitor, compound 3 (MS31). Compound 3 potently inhibited binding of trimethyllysine-containing peptides

  通过筛选表观遗传化合物库，我们确定了UNC0638（组蛋白甲基转移酶G9a和GLP的强效抑制剂）是SPIN1（spindlin 1）（一种甲基赖氨酸阅读器蛋白）的弱抑制剂。我们对这种微弱打击的优化导致发现了一种有效的，选择性的，具有细胞活性的SPIN1抑制剂化合物3（MS31 ）。化合物3有效抑制含三甲基赖氨酸的肽与SPIN1的结合，表现出高结合亲和力，对SPIN1的选择性高于其他表观遗传的读者和作者，直接将SPIN1结合在细胞中，并且对非致瘤细胞无毒。SPIN1-化合物3的晶体结构复合体表明它选择性地结合了SPIN1的Tudor域II。我们还设计了结构相似但无活性的化合物4（MS31N）作为阴性对照。我们的结果首次证明，通过靶向单个Tudor结构域可以产生有效的，选择性的和细胞活性片段样抑制剂。
• Structural Requirements for Factor Xa Inhibition by 3-Oxybenzamides with Neutral P1 Substituents:  Combining X-ray Crystallography, 3D-QSAR, and Tailored Scoring Functions
  作者：Hans Matter、David W. Will、Marc Nazaré,、Herman Schreuder、Volker Laux、Volkmar Wehner

  DOI：10.1021/jm049187l

  日期：2005.5.1

  The design, synthesis, and structure-activity relationship of 3-oxybenzamides as potent inhibitors of the coagulation protease factor Xa are described on the basis of X-ray structures, privileged structure motifs, and SAR information. A total of six X-ray structures of fXa/inhibitor complexes led us to identify the major protein-ligand interactions. The binding mode is characterized by a lipophilic dichlorophenyl substituent interacting with Tyr228 in the protease S1 pocket, while polar parts are accommodated in S4. This alignment in combination with docking allowed derivation of 3D-QSAR models and tailored scoring functions to rationalize biological affinity and provide guidelines for optimization. The resulting models showed good correlation coefficients and predictions of external test sets. Furthermore, they correspond to binding site topologies in terms of steric, electrostatic, and hydrophobic complementarity. Two approaches to derive tailored scoring functions combining binding site and ligand information led to predictive models with acceptable predictions of the external set. Good correlations to experimental affinities were obtained for both AFMoC (adaptation of fields for molecular comparison) and the novel TScore function. The SAR information from 3D-QSAR and tailored scoring functions agrees with all experimental data and provides guidelines and reasonable activity estimations for novel fXa inhibitors.
• 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：——
• Brominated phenylalanines
  作者：M. L. Anhoury、P. Crooy、R. De Neys、J. Eliaers

  DOI：10.1002/bscb.19740830304

  日期：——

  Abstract(3‐(3‐Bromo‐4‐hydroxy‐S‐methoxy‐phenyl)alanine (Ie) exerts a long‐acting antihypertensive effect in rats and dogs : its synthesis and its optical resolution have already appeared in the literature. 1 Ten new mono‐ and polybrominated phenylalanines with hydroxy‐ and/or methoxy‐groups are here described. These unnatural amino‐acide were synthesized by direct bromination, or via the acetamidomalonic esters (V), or via the azlactones (VI) and the corresponding phenylpyruvic acids (VIII).
• 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。

表征谱图