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7-methoxy-4(H)-oxo-1-benzopyran-2-carboxylic acid | 23915-78-8

中文名称
——
中文别名
——
英文名称
7-methoxy-4(H)-oxo-1-benzopyran-2-carboxylic acid
英文别名
7-methoxy-4-oxo-4H-1-benzopyran-2-carboxylic acid;7-methoxy-4-oxo-4H-chromene-2-carboxylic acid;7-methoxy-4-oxo-4H-chromene-2-carboxylic acid;7-Methoxy-4-oxo-4H-chromen-2-carbonsaeure;7-methoxychromone-2-carboxylic acid;7-Methoxy-chromon-carbonsaeure-(2);7-methoxy-4-oxochromene-2-carboxylic acid
7-methoxy-4(H)-oxo-1-benzopyran-2-carboxylic acid化学式
CAS
23915-78-8
化学式
C11H8O5
mdl
MFCD00847041
分子量
220.182
InChiKey
HJDIJMAWNXZWFJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.6
  • 重原子数:
    16
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.09
  • 拓扑面积:
    72.8
  • 氢给体数:
    1
  • 氢受体数:
    5

安全信息

  • 海关编码:
    2918990090

SDS

SDS:05ca0ee6484ef04be02cb48b531f6de3
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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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Optimization of Chromone-2-carboxamide Melanin Concentrating Hormone Receptor 1 Antagonists:  Assessment of Potency, Efficacy, and Cardiovascular Safety
    摘要:
    Evaluation of multiple structurally distinct series of melanin concentrating hormone receptor 1 antagonists in an anesthetized rat cardiovascualar assay led to the identification of a chromone-2-carboxamide series as having excellent safety against the chosen cardiovascular endpoints at high drug concentrations in the plasma and brain. Optimization of this series led to considerable improvements in affinity, functional potency, and pharmacokinetic profile. This led to the identification of a 7-fluorochromone-2-carboxamide (22) that was orally efficacious in a diet-induced obese mouse model, retained a favorable cardiovascular profile in rat, and demonstrated dramatic improvement in effects on mean arterial pressure in our dog cardiovascular model compared to other series reported by our group. However, this analogue also led to prolongation of the QT interval in the dog that was linked to affinity for hERG channel and unexpectedly potent functional blockade of this ion channel.
    DOI:
    10.1021/jm060683e
  • 作为产物:
    描述:
    丹皮酚sodium碳酸氢钠potassium carbonate 作用下, 以 乙醇丙酮 为溶剂, 反应 6.0h, 生成 7-methoxy-4(H)-oxo-1-benzopyran-2-carboxylic acid
    参考文献:
    名称:
    含有酰胺基的色酮衍生物的合成、抗炎活性和构象关系研究
    摘要:
    炎症是免疫系统对感染、损伤或刺激等各种刺激的最初生物反应。广泛的研究表明,越来越多的疾病是由炎症机制引发的。目前,抗炎药物因其治疗优势而广泛应用于临床。然而,我们也不能忽视潜在的副作用。本工作采用联合药物设计原理,设计合成了一系列以色酮为母核的酰胺类化合物。生物学评价结果表明,与阳性药物布洛芬相比,四种化合物表现出较低的EC 50值。值得注意的是,化合物5-9 对 RAW264.7 细胞中脂多糖 (LPS) 诱导的一氧化氮 (NO) 的产生表现出最佳的抑制活性 (EC 50 = 5.33 ± 0.57 μM)。构效关系(SAR)表明,色酮母核5位和8位吸电子基团或6位和7位给电子基团的存在可以增强色酮的抗炎活性。分子对接研究预测了化合物与蛋白质之间的相互作用模式。此外,这些研究表明酰胺键是抗炎作用的关键基团。根据上述研究的总结,可以推断化合物5-9具有作为抗炎药物的潜力,值得进一步研究。
    DOI:
    10.1016/j.bmcl.2023.129539
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文献信息

  • Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor
    申请人:Lynch K. John
    公开号:US20050209274A1
    公开(公告)日:2005-09-22
    The present invention is directed to compounds of formula (I), which antagonize of the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor which is useful for the prevention or treatment of eating disorders, weight gain, obesity, abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders.
    本发明涉及式(I)的化合物,通过对抗黑素浓集激素(MCH)的作用,通过对抗黑素浓集激素受体,有助于预防或治疗进食障碍、体重增加、肥胖、生殖和性行为异常、甲状腺激素分泌、利尿和水/电解质稳态、感觉处理、记忆、睡眠、觉醒、焦虑、抑郁、癫痫、神经退行性疾病和精神障碍。
  • A Selective and Versatile Synthesis of Substituted Chromones via Addition of Phenols to Dimethyl Acetylenedicarboxylate
    作者:MJ Stoermer、DP Fairlie
    DOI:10.1071/ch9950677
    日期:——

    Despite many published syntheses of chromones, none has been reported to be both selective for chromones and tolerant of ring substitution. The addition of substituted phenols to dimethyl acetylenedicarboxylate is now reported as a versatile high yield initial step in a simple three-step synthesis of chromone 2-carboxylic acids. Triethylamine being used to deprotonate the substituted phenol, the addition to dimethyl acetylenedicarboxylate proceeds under mild conditions and tolerates a wide range of functional groups on the phenol. Although not stereoselective, both fumarate and maleate aryloxy products of this addition can then be cyclized, according to a known method, to chromones without contamination by isomeric coumarins. Thus the addition reaction is a valuable component of a versatile and selective synthesis of substituted chromones.

    尽管已发表了许多色酮的合成方法,但还没有任何一种方法既对色酮具有选择性,又对环的取代具有耐受性。现在有报道称,将取代苯酚加到乙炔二甲酸二甲酯上是一种多功能的高产率初始步骤,可简单地三步合成铬酮 2-羧酸。使用三乙胺对取代的苯酚进行去质子化,与乙炔二甲酸二甲酯的加成反应在温和的条件下进行,并可容忍苯酚上的多种官能团。虽然不具有立体选择性,但根据已知的方法,这种加成反应的富马酸酯和马来酸酯芳氧基产物都可以环化成色酮,而不会受到异构香豆素的污染。因此,该加成反应是取代色酮的多功能选择性合成的重要组成部分。
  • [EN] SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY<br/>[FR] CYCLOLALKYLES SUBSTITUÉS EN TANT QUE MODULATEURS DE LA VOIE DE STRESS INTÉGRÉE
    申请人:CALICO LIFE SCIENCES LLC
    公开号:WO2020223536A1
    公开(公告)日:2020-11-05
    Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.
    本文提供了用于调节综合应激反应(ISR)并治疗相关疾病、疾病和症状的化合物、组合物和方法。
  • [EN] ANTI-INFECTIVE AGENTS<br/>[FR] AGENTS ANTI-INFECTIEUX
    申请人:UNIV DUNDEE
    公开号:WO2017221002A1
    公开(公告)日:2017-12-28
    The present invention relates to a novel class of chromene-2-carboxamide compounds inhibitors of general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8 and X are as defined herein, to their use in medicine, and their use as anti-infective agents in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.
    本发明涉及一类新型的基于色酮-2-羧酰胺化合物的抑制剂,其通式为(I),其中R1、R2、R3、R4、R5、R6、R7、R8和X如本文所定义,其在医学上的用途,特别是作为抗感染剂的用途,包括含有它们的组合物,其制备过程以及用于这些过程的中间体。
  • Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-Up the Discovery of Chromone-Based Multitarget-Directed Ligands
    作者:Cagide、Oliveira、Reis、Borges
    DOI:10.3390/molecules24234214
    日期:——
    obtained with good yields (54–93%). Only in the case of the nitro substituent (compound 11B), an ester was obtained instead of the desired carboxylic acid. Following this synthetic route chromone carboxylic acids can be attained with a high degree of purity, without the need of the tedious and expensive purification processes through column chromatography. The reaction is safe, cost-effective, fast and robust
    6-溴色酮-2-羧酸 (3) 是通过微波辅助工艺合成的。反应的优化通过不同的参数进行,例如碱类型/试剂当量数、溶剂、温度和反应时间。反应产率提高到87%。新的合成路线是通用的,因为以良好的产率 (54-93%) 获得了几种色酮-2-羧酸(化合物 4B-10B)。仅在硝基取代基(化合物 11B)的情况下,获得酯而不是所需的羧酸。按照这种合成路线,色酮羧酸可以以高纯度获得,而无需通过柱色谱进行繁琐和昂贵的纯化过程。反应安全、经济、快速、稳健,可用于基于chromone scaffold的简洁、面向多样性的文库开发。整个研究可以看作是加快发现基于色酮的多靶标配体的一步。
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