5-甲氧基-2,3-二苯并呋喃-3-乙酸 | 93198-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 5-甲氧基-2,3-二苯并呋喃-3-乙酸
• 英文名称: (+/-)-(2,3-dihydro-5-methoxybenzofuran-3-yl)acetic acid
• 英文别名: 5-methoxy-2,3-dihydro-3-benzofuranacetic acid；5-Methoxy-2,3-dihydro-1-benzofuran-3-acetic acid；2-(5-methoxy-2,3-dihydro-1-benzofuran-3-yl)acetic acid
• CAS: 93198-71-1
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: NZHDKXOGTJCWHE-UHFFFAOYSA-N

物化性质

• 熔点：
  114 °C
• 沸点：
  359.3±35.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2,3-二苯并呋喃-3-乙酸 在 dirhodium tetraacetate 、 草酰氯 、 4 A molecular sieve 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  取代萘并呋喃为致幻剂苯乙胺-麦角灵杂合分子，具有意想不到的毒蕈碱拮抗活性。

  摘要：

  合成了一系列取代的消旋萘并呋喃，作为两种主要的典型致幻药物类别（苯乙胺和色胺/麦角灵）的“混合”分子。尽管据推测这些新药可能对5-羟色胺5-HT2A / 2C受体亚型具有很高的亲和力，但仍观察到了对毒蕈碱受体的出乎意料的亲和力。最初合成用于本研究的化合物为（+/-）-抗-和合成-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘[1,8-bc]呋喃（4a ，b）和它们的8-溴衍生物4c，d。首先在训练中区分盐水与LSD酒石酸盐（0. 08 mg / kg）的大鼠中，分析了溴化伯胺4c，d在双杠杆药物歧视（DD）范式中的活性。还有4c 评估d在克隆的人5-HT 2A，5-HT 2B和5-HT 2C受体上与激动剂和拮抗剂放射性配体竞争的能力。在这些初步分析中发现顺式非对映异构体具有最高活性后，N-烷基化类似物syn-N，N-N-二甲基-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘并[1

  DOI：

  10.1021/jm980076u
• 作为产物：
  描述：

  2,5-二甲氧基苯甲酸 在 palladium on activated charcoal 氢氧化钾 、 草酰氯 、 氢气 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 乙醇 、 甲苯 、 苯 为溶剂， 反应 88.5h， 生成 5-甲氧基-2,3-二苯并呋喃-3-乙酸
  参考文献：
  名称：

  取代萘并呋喃为致幻剂苯乙胺-麦角灵杂合分子，具有意想不到的毒蕈碱拮抗活性。

  摘要：

  合成了一系列取代的消旋萘并呋喃，作为两种主要的典型致幻药物类别（苯乙胺和色胺/麦角灵）的“混合”分子。尽管据推测这些新药可能对5-羟色胺5-HT2A / 2C受体亚型具有很高的亲和力，但仍观察到了对毒蕈碱受体的出乎意料的亲和力。最初合成用于本研究的化合物为（+/-）-抗-和合成-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘[1,8-bc]呋喃（4a ，b）和它们的8-溴衍生物4c，d。首先在训练中区分盐水与LSD酒石酸盐（0. 08 mg / kg）的大鼠中，分析了溴化伯胺4c，d在双杠杆药物歧视（DD）范式中的活性。还有4c 评估d在克隆的人5-HT 2A，5-HT 2B和5-HT 2C受体上与激动剂和拮抗剂放射性配体竞争的能力。在这些初步分析中发现顺式非对映异构体具有最高活性后，N-烷基化类似物syn-N，N-N-二甲基-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘并[1

  DOI：

  10.1021/jm980076u

文献信息

• CNS affecting 5-oxy-3-aminomethyl-dihydro-benzofurans and benzothiophenes
  申请人：H. Lundbeck A/S

  公开号：US04847254A1

  公开（公告）日：1989-07-11

  The present invention relates to 3-aminomethyl derivatives of indane, dihydrobenzofurane, dihydrobenzothiophene, and indoline, acid addition salts thereof, isomers thereof, methods of preparation, pharmaceutical compositions and method of treating CNS-disorders such as schizophrenia, Parkinson's disease, depression, anxiety, migraine and senile dementia, or in the cure of cardiovascular diseases, by administering such a derivative.

  本发明涉及吲烷、二氢苯并呋喃、二氢苯并噻吩和吲哚啉的3-氨基甲基衍生物，其酸加成盐、异构体、制备方法、药物组合物以及通过施用此类衍生物治疗中枢神经系统疾病如精神分裂症、帕金森病、抑郁症、焦虑症、偏头痛和老年痴呆症，或在治疗心血管疾病中的方法。
• Production and Selection of Antibody–Antigen Pairs for the Development of Immunoenzyme Assay and Lateral Flow Immunoassay Methods for Carbofuran and Its Analogues
  作者：Yuxiang Wu、Qi Fan、Yinuo Chen、Xia Sun、Guoqing Shi

  DOI：10.3390/bios12080560

  日期：——

  To produce a sensitive monoclonal antibody (mAb) for the simultaneous detection of carbofuran, benfuracarb, carbosulfan and 3-hydroxy-carbofuran, 2,3-dihydro-2,2-dimethyl-7-benzofuranmethanamine (DDB) was conjugated to bovine serum albumin (BSA) to prepare the immunogen DDB-BSA and mice were immunized. Coating antigens were prepared by conjugating DDB and 5-methoxy-2,3-dihydrobenzofuran-3-acetic acid (MDA) to BSA and ovalbumin (OVA), respectively. Furthermore, the effect of different antibody–antigen pairs on the sensitivity of ELISA and LFIA methods for the detection of carbofuran was investigated. After the immunization, a high-affinity mAb 13C8 was obtained. The ability of the coating antigen to compete with carbofuran for binding antibodies was found to be significantly different between ELISA and LFIA methods. With the antibody–antigen pair 13C8-MDA-OVA, the IC50 values of the ELISA and QD-LFIA methods for carbofuran were 0.18 ng/mL and 0.67 ng/mL, respectively. The cross-reactivity (CR) values of the two methods for benfuracarb, carbosulfan and 3-hydroxy-carbofuran ranged from 72.0% to 83.7%, while, for other carbamate pesticides, the CR values were less than 1%. The spiked recoveries of carbofuran in vegetables by the QD-LFIA method were 83–111%, with a coefficient of variation below 10%, and the test results of the actual samples were consistent with the HPLC-MS method. Overall, this study provides key materials for the development of immunoassays for carbofuran and its analogues, and the antibody–antigen pair selection strategy established in this study provides useful insights for the development of sensitive immunoassays for other compounds.

  为了制备一种同时检测呋喃丹、苯呋喃丹、多菌灵和 3-羟基呋喃的灵敏单克隆抗体（mAb），将 2,3-二氢-2,2-二甲基-7-苯并呋喃甲胺（DDB）与牛血清白蛋白（BSA）共轭，制备出免疫原 DDB-BSA，并对小鼠进行免疫。将 DDB 和 5-甲氧基-2,3-二氢苯并呋喃-3-乙酸（MDA）分别与 BSA 和卵清蛋白（OVA）共轭制备包被抗原。此外，还研究了不同抗体抗原对 ELISA 和 LFIA 方法检测呋喃丹灵敏度的影响。免疫后，获得了高亲和性 mAb 13C8。研究发现，包被抗原与呋喃丹竞争结合抗体的能力在 ELISA 和 LFIA 方法中存在显著差异。对于抗体抗原对 13C8-MDA-OVA，ELISA 和 QD-LFIA 方法对呋喃丹的 IC50 值分别为 0.18 纳克/毫升和 0.67 纳克/毫升。对于苯呋喃丹、多菌灵和 3-羟基呋喃丹，两种方法的交叉反应值为 72.0%至 83.7%，而对于其他氨基甲酸酯类农药，交叉反应值则低于 1%。QD-LFIA方法对蔬菜中呋喃丹的加标回收率为83%-111%，变异系数低于10%，实际样品的检测结果与HPLC-MS方法一致。总之，本研究为开发克百威及其类似物的免疫分析方法提供了关键材料，同时本研究建立的抗体-抗原配对选择策略为开发其他化合物的灵敏免疫分析方法提供了有益的启示。
• 3-Aminomethyl derivatives of indane, indoline and dihydrobenzofurane and dihydrobenzothiophene
  申请人：H. LUNDBECK A/S

  公开号：EP0281261A2

  公开（公告）日：1988-09-07

  Indane-, dihydrobenzofurane-, dihydrobenzothiophene-, and indoline- derivatives of the following formula: wherein X, R¹, R², R³ and R⁴ are as defined in Claim 1, are effective at presynaptic DA receptors, or both at pre- and postsynaptic DA receptors, indicating usefulness in the treatment of disorders of the central nervous system (CNS) such as schizophrenia or Parkinson's disease. The 1-aminomethyl derivatives of Formula I exist as optical isomers, and the useful effects are often found in the single enantiomers to a different degree. A method for the preparation of compounds of Formula I is described.

  下式中的茚满-、二氢苯并呋喃-、二氢苯并噻吩-和吲哚啉-衍生物： 其中X、R¹、R²、R³和R⁴如权利要求1中所定义，对突触前DA受体有效，或对突触前和突触后DA受体均有效，表明在治疗精神分裂症或帕金森病等中枢神经系统（CNS）疾病方面有用。 式I的1-氨基甲基衍生物以光学异构体形式存在，其有用的效果通常在单一对映体中以不同程度存在。 描述了一种制备式I化合物的方法。
• Electron impact mass spectrometry of some 2,3-dihydro-1-benzofuran-3-acetic acids
  作者：Pierfrancesco Bravo、Calimero Ticozzi、Sergio Daolio、Pietro Traldi、Enrico Vecchi

  DOI：10.1002/oms.1210200112

  日期：1985.1

  AbstractThe mass spectrometric behaviour of four 2,3‐dihydro‐1‐benzofuran‐3‐acetic acids has been studied in detail with the aid of exact mass measurements, linked scans, collisionally activated decomposition, mass analysed ion kinetic energy spectra and labelling experiments. Unusual fragmentation pathways are emphasized for which mechanisms are proposed.
• Synthesis and Pharmacological Characterization of a Series of Geometrically Constrained 5-HT_2A/2C Receptor Ligands
  作者：James J. Chambers、Jason C. Parrish、Niels H. Jensen、Deborah M. Kurrasch-Orbaugh、Danuta Marona-Lewicka、David E. Nichols

  DOI：10.1021/jm030064v

  日期：2003.7.1

  In studies of the SAR of phenethylamine-type serotonin 5-HT2A receptor agonists, substituted conformationally constrained tetrahydronaphthofurans were designed to investigate the optimal conformation of the 2-aminoethyl moiety. These compounds were tested using in vitro assays for affinity at 5-HT1A, 5-HT2A, and 5-HT2C receptors. The benzofuran-containing analogues, 6a and 6b, had significantly higher affinity for the 5-HT receptors tested than did the benzodi-hydrofuran-containing compounds, 4a, 4b, 5a, and 5b. The most potent compound (8-bromo-6-methoxy-4,5-dihydro-3H-naphtho[1,8-bc]furan-5-yl)aminomethane, 6b, had K-i values for displacement of [I-125] -DOI from 5-HT2A and 5-HT2C cloned rat receptors of 2.6 and 1.1 nM, respectively. Despite their high affinity, the compounds of this naphthofuran series lacked high intrinsic activity at the 5-HT2A receptor as measured using the phosphoinositide hydrolysis assay. The most potent compound in vitro, 6b, was tested in the two-lever drug discrimination assay in rats trained to discriminate LSD from saline, and failed to substitute, a result typical for compounds with low intrinsic activity. Thus, although conformational constraint has led to high-affinity 5-HT2A ligands with partial agonist activity, all of the spatial and steric properties of the ligand necessary for full receptor activation have not yet been identified.