7-甲氧基-4-氧代苯并吡喃-2-羧酸乙酯 | 38322-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 7-甲氧基-4-氧代苯并吡喃-2-羧酸乙酯
• 英文名称: ethyl 7-methoxy-4-oxo-4H-chromene-2-carboxylate
• 英文别名: 4H-1-Benzopyran-2-carboxylic acid, 7-methoxy-4-oxo-, ethyl ester；ethyl 7-methoxy-4-oxochromene-2-carboxylate
• CAS: 38322-74-6
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: QBQCROLDTZVZHW-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  381.5±42.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 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：

  7-甲氧基-4-氧代苯并吡喃-2-羧酸乙酯 在 palladium on activated charcoal 锂硼氢 、 四溴化碳 、 氢气 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 25.0~100.0 ℃ 、344.73 kPa 条件下， 反应 136.0h， 生成 3-(7-Methoxy-chroman-2-ylmethyl-amino)-propanol
  参考文献：
  名称：

  New Generation Dopaminergic Agents. 1. Discovery of a Novel Scaffold Which Embraces the D₂ Agonist Pharmacophore. Structure−Activity Relationships of a Series of 2-(Aminomethyl)chromans

  摘要：

  A series of 2-(aminomethyl)chromans (2-AMCs) was synthesized and evaluated for their affinity and selectivity for both the high-and low-affinity agonist states (D-2(High) and D-2(Low), respectively) of the dopamine (DA) D-2 receptor. The 7-hydroxy-2-(aminomethyl)chroman moiety was observed to be the primary D-2 agonist pharmacophore. The 2-methylchroman moiety was discovered to be an entirely novel scaffold which could be used to access the D-2 agonist pharmacophore. Attaching various simple alkyl and arylalkyl side chains to the 7-hydroxy 2-AMC nucleus had significant effects on selectivity for the D-2(High) receptor vs the 5HT(1A) and alpha(1) receptors. A novel DA partial agonist, (R)-(-)-2-(benzylamino)methyl)chroman-7-ol [R-(-)-35c], was identified as having the highest affinity and best selectivity for the D-2(High) receptor vs the alpha(1) and 5HT(1A) receptors. Several regions of the 2-AMC nucleus were modified and recognized as potential sites to modulate the level of intrinsic activity. The global minimum conformer of the 7-hydroxy-2-AMC moiety was identified as fulfilling the McDermed model D-2 agonist pharmacophoric criteria and was proposed as the D-2 receptor-bound conformation. Structure-activity relationships gained from these studies have aided in the synthesis of D-2 partial agonists of varying intrinsic activity levels. These agents should be of therapeutic value in treating disorders resulting from hypo-and hyperdopaminergic activity, without the side effects associated with complete D-2 agonism or antagonism.

  DOI：

  10.1021/jm9703653
• 作为产物：
  描述：

  4-(2-hydroxy-4-methoxy-phenyl)-2,4-dioxo-butyric acid ethyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以1.04 g的产率得到7-甲氧基-4-氧代苯并吡喃-2-羧酸乙酯
  参考文献：
  名称：

  仿生型方法用于木酮缩醛的三环核。适用于短促立体合成的白蛋白的合成，以及木糖酮G的首次合成

  摘要：

  描述了一种简便的方法来制备木酮缩醛的线性四氢呋喃苯并吡喃环系统。苯甲醇的原酸酯克莱森重排和分子内阳离子环化是合成中的关键步骤。利用这种策略，实现了短时，立体控制和高收率的植物毒性代谢物白蛋白的合成。的路易斯酸的唯一情况下催化的异构化外延-alboatrin到alboatrin进行了观察。随后该方法延长了xyloketal G，其中三个步骤即的一锅反应，乙酰化，异构化和脱甲基化的去甲混合物的乙酰化过程中出现的第一个全合成ö甲基xyloketal G和去甲ö甲基EPI在AlCl 3存在下木酮基G以非常好的总产率提供木酮基G。

  DOI：

  10.1016/j.tet.2011.04.084

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。
• [EN] SUBSTITUTED CHROMANES AND METHOD OF USE<br/>[FR] CHROMANES SUBSTITUÉS ET MÉTHODE D'UTILISATION
  申请人：ABBVIE INC

  公开号：WO2016069757A1

  公开（公告）日：2016-05-06

  The invention provides for compounds of formula (I), wherein R1, X, Y, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, m, and R" have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions mediated and modulated by CFTR, including cystic fibrosis, Sjögren's syndrome, pancreatic insufficiency, chronic obstructive lung disease, and chronic obstructive airway disease. Also provided are pharmaceutical compositions comprised of one or more compounds of formula (I).

  该发明提供了一种公式（I）化合物，其中R1、X、Y、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、m和R"具有规范中定义的任何值，以及其药学上可接受的盐，这些化合物在治疗由CFTR介导和调节的疾病和症状中是有用的，包括囊性纤维化、Sjögren综合征、胰腺功能不全、慢性阻塞性肺病和慢性阻塞性气道疾病。还提供了由一个或多个公式（I）化合物组成的药物组合物。
• [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。
• Synthesis and evaluation of chromone-2-carboxamido-alkylamines as potent acetylcholinesterase inhibitors
  作者：Paptawan Suwanhom、Teerapat Nualnoi、Pasarat Khongkow、Vannajan Sanghiran Lee、Luelak Lomlim

  DOI：10.1007/s00044-020-02508-5

  日期：2020.3

  proposed to be associated with reduced levels of the neurotransmitter acetylcholine (ACh). Cholinesterase enzymes, namely acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) cleave ACh via hydrolysis. Cholinesterase inhibitors (ChEIs) are the main group of drugs currently used for the treatment of AD. Novel chromone-2-carboxamido-alkylamines (7–18) were designed, synthesized, and evaluated for

  阿尔茨海默氏病（AD）被认为是全球最大的公共负担之一。AD的病理生理学被认为与神经递质乙酰胆碱（ACh）水平的降低有关。胆碱酯酶，即乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）通过水解裂解ACh。胆碱酯酶抑制剂（ChEIs）是目前用于治疗AD的主要药物。新的色酮-2-甲酰氨基烷基胺（7 - 18）被设计，合成并评价了胆碱酯酶抑制活性。这些化合物在微摩尔范围内显示出有效的AChE抑制活性（IC 50为0.09-9.16 µM），并显示出较弱的BChE抑制活性（IC 50为12.09-44.56 µM）。化合物14（IC 50 0.09±0.02 µM）是该系列中最有效的AChEI；它显示出比临床使用的他克林更高的活性。酶动力学研究表明14是一种非竞争性抑制剂。分子对接研究显示14是一种双结合位点抑制剂。化合物14对SH-SY5Y细胞没有诱导任何浓度相关的细胞毒性作用。它还在细胞系中显示
• USE OF POLYPHOSPHORIC ACID IN THE HYDROLYSIS OF CHROMONE ESTERS
  作者：Xungui He、Zhiyu Li、Qidong You

  DOI：10.1081/scc-120002508

  日期：2002.1.1

  ABSTRACT Hydrolysis of esters was achieved in fairly high yield (59–98%) using polyphosphoric acid (PPA). The reagent was particularly useful for the hydrolysis of chromone side chain esters without ring opening.

  摘要 使用多磷酸 (PPA) 以相当高的产率 (59–98%) 实现酯的水解。该试剂特别适用于色酮侧链酯的水解而无需开环。