5-carbomethoxy-6-hydroxysalicylaldehyde | 39503-26-9

• 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: 5-carbomethoxy-6-hydroxysalicylaldehyde
• 英文别名: 3-formyl-2,4-dihydroxy-benzoic acid methyl ester；2.4-Dihydroxy-isophthalaldehydsaeure-methylester；3-Formyl-2,4-dihydroxy-benzoesaeure-methylester；methyl 2,4-dihydroxy-3-formylbenzoate；3-Formyl-2,4-dihydroxybenzoesaeuremethylester；3-Formyl-β-resorcylsaeure-methylester；methyl 3-formyl-2,4-dihydroxybenzoate
• CAS: 39503-26-9
• 化学式: C₉H₈O₅
• 分子量: 196.16
• InChiKey: YYUAKVMGFMRTGB-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  285.6±40.0 °C(Predicted)
• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  5-carbomethoxy-6-hydroxysalicylaldehyde 在 sodium hydroxide 作用下， 生成 2,6-二羟基苯甲醛
  参考文献：
  名称：

  340. γ 3'-取代的间苯二酚核。第一部分：γ-间苯二醛的合成

  摘要：

  DOI：

  10.1039/jr9380001828
• 作为产物：
  描述：

  2,4-二羟基苯甲酸甲酯 、 氰化锌 在 盐酸 、 三氯化铝 作用下， 以 苯 为溶剂， 以23%的产率得到5-carbomethoxy-6-hydroxysalicylaldehyde
  参考文献：
  名称：

  2-硝基苯并[b]呋喃的抗菌活性和极谱半波降低潜力。

  摘要：

  一系列2-硝基苯并[b]呋喃衍生物对金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌、鼠伤寒沙门氏菌、肠炎沙门氏菌、弗氏志贺菌、普通变形杆菌或铜绿假单胞菌的抗菌活性在体外被测定。大多数化合物对这些细菌显示出显著的活性，除了普通变形杆菌和铜绿假单胞菌，它们中的一种对金黄色葡萄球菌的活性大约是呋喃西林的30倍。单甲氧基和二甲氧基衍生物（2a, 3a, 4a, 5f）最为活跃。在pH 7时，2-硝基苯并[b]呋喃的极谱半波电位（E1/2）在一个狭窄的范围内，为-0.450±0.04 V，而区域异构的硝基苯并[b]呋喃的E1/2值更为负（-0.560至-0.726 V）。对于2-硝基苯并[b]呋喃来说，苯环上的取代基对2-硝基基团的还原电位几乎没有影响，然而抗菌活性明显取决于取代基团。

  DOI：

  10.1248/cpb.33.2854

文献信息

• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES, À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2011015241A1

  公开（公告）日：2011-02-10

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT2B (5-HT2B receptor), and on the prostaglandin F2 • receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

  构象受限、空间定义的12-30元大环环系统(I型)由三个不同的构建模块组成：芳香模板a、构象调节剂b和间隔基团c，详细描述在说明书和专利要求中。I型大环可通过并行合成或组合化学方法轻松制备。它们设计用于与特定生物靶点相互作用。特别是，它们在胃动素受体(MR受体)、5-羟色胺受体亚型5-HT2B(5-HT2B受体)和前列腺素F2•受体(FP受体)上显示激动或拮抗活性。因此，它们潜在用于治疗胃肠道低动力障碍，如糖尿病性胃轻瘫和便秘型肠易激综合征；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；眼压增高，如青光眼和早产。
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Obrecht Daniel

  公开号：US20120270881A1

  公开（公告）日：2012-10-25

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of formulae Ia and Ib are constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. These macrocycles Ia and Ib are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being the agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), ion channels and signal transduction pathways. In particular, these macrocycles act as antagonists of the motilin receptor, the FP receptor and the purinergic receptors P2Y 1 , as modulators of the serotonin receptor of subtype 5-HT 2B , as blockers of the voltage-gated potassium channel K v 1.3 and as inhibitors of the β-catenin-dependent “canonical” Wnt pathway. Thus they are showing great potential as medicaments for a variety of diseases.

  具有结构限制的、空间定义的12-30环的大环系统Ia和Ib由三个不同的分子部分构成：模板A、构象调节剂B和桥C。这些大环Ia和Ib可以通过并行合成或溶液中或固相上的组合化学来轻松制备。它们被设计用于与各种特定的生物靶标类相互作用，例如对G蛋白偶联受体（GPCRs）、离子通道和信号转导途径的激动或拮抗活性。特别地，这些大环作为莫蒂林受体的拮抗剂、FP受体和嘌呤受体P2Y1的调节剂、5-HT2B亚型的5-羟色胺受体的调节剂、电压门控钾通道Kv1.3的阻断剂以及β-连环蛋白依赖的“经典”Wnt途径的抑制剂。因此，它们显示出作为各种疾病药物的巨大潜力。
• Synthetic Studies on the Benzofuran Derivatives. II. Reactions of Aromatic o-Hydroxyaldehyde Derivatives and Ethyl Bromomalonate
  作者：Takashi Matsumoto、Kenji Fukui

  DOI：10.1246/bcsj.30.3

  日期：1957.1

  ne (V) and 2,2-dicarbethoxy-3-hydroxy-6-benzyloxycoumaran (XII) were synthesized respectively from 2,6-dihydroxy-3-carbomethoxybenzaldehyde (IV) or 4-benzyloxy-2-hydroxybenzaldehyde (X) and ethyl bromomalonate by the method of Tanaka for benzofuran synthesis. 2-Carbethoxy-4-hydroxy-5-carbomethoxycoumarone (V) was hydrolysed to 4-hydroxycoumarone-2,5-dicarboxylic acid (VI). This dibasic acid VI was

  2-Carbethoxy-4-hydroxy-5-carbomethoxycoumarone (V) 和 2,2-dicarbethoxy-3-hydroxy-6-benzyloxycoumaran (XII) 分别由 2,6-dihydroxy-3-carbomethoxybenzaldehyde (IV) 或 4-苯甲氧基-2-羟基苯甲醛(X)和溴丙二酸乙酯通过Tanaka的方法合成苯并呋喃。2-Carbethoxy-4-hydroxy-5-carbomethoxycoumarone (V) 被水解成 4-hydroxycoumarone-2,5-二羧酸 (VI)。这种二元酸 VI 在喹啉中用铜粉脱羧成卡兰卓尔 (VIII) 和卡兰吉酸 (IX) 的混合物。2,2-Dicarbethoxy-3-hydroxy-6-benzyloxy-coumaran (XII) 被水解成 6-benzyloxycoumarone-2-
• Pharmaceutical ethers
  申请人：Burroughts Wellcome Co.

  公开号：US04410537A1

  公开（公告）日：1983-10-18

  This invention is directed to novel ether compounds of formula (I) ##STR1## which are of value in medicine in the palliation of haemoglobinopathies, in particular sickle-cell anaemia, and also in the palliation of pulmonary dysfunction, protection from the effects of hypoxia and the radio-sensitization of tumors. The invention is also directed to methods for the preparation of the ether compounds, to pharmaceutical formulations containing them, the preparation of such formulations and the use of the compounds in human medicine. Also provided by the invention are intermediates of value in the preparation of the ether compounds, by the methods described, and the preparation of the intermediates.

  该发明涉及一种新型醚类化合物，化学式为（I）##STR1## 这些化合物在医学上具有价值，用于缓解血红蛋白病，特别是镰状细胞贫血，以及缓解肺功能障碍，保护免受低氧影响，以及增强肿瘤的放射敏感性。该发明还涉及制备这些醚类化合物的方法，包含它们的药物配方，这些配方的制备以及在人类医学中使用这些化合物。该发明还提供了在制备醚类化合物中具有价值的中间体，通过所述方法制备这些中间体。
• Substituted phenol ethers, their preparation, intermediates therefor, pharmaceutical compositions containing them and the preparation thereof
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0022229A1

  公开（公告）日：1981-01-14

  This invention is directed to novel ether compounds of formula which are of value in medicine in the palliation of haemo- giobinopathies, in particular sickle-cell anaemia, and also in the palliation of pulmonary dysfunction, protection from the effects of hypoxia and the radio-sensitization of tumours. The invention is also directed to methods for the preparation of the ether compounds, to pharmaceutical formulations containing them, the preparation of such formulations and the use of the compounds in human medicine. Also provided by the invention are intermediates of value in the preparation of the ether compounds, by the methods described, and the preparation of the intermediates.

  本发明涉及具有以下式的新型醚化合物，该化合物在医学上对缓解血红蛋白病，特别是镰状细胞贫血，以及缓解肺功能障碍、保护免受低氧影响和放射敏化肿瘤方面具有价值。本发明还涉及制备醚化合物的方法，包含它们的制药配方，以及在人类医学中使用这些化合物的方法。本发明还提供了在制备醚化合物的过程中有价值的中间体，以及制备这些中间体的方法。