6-甲基-苯并呋喃-2-羧酸 | 50779-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 6-甲基-苯并呋喃-2-羧酸
• 英文名称: 6-methylbenzofuran-2-carboxylic acid
• 英文别名: 6-methyl-1-benzofuran-2-carboxylic acid
• CAS: 50779-65-2
• 化学式: C₁₀H₈O₃
• mdl: MFCD08059102
• 分子量: 176.172
• InChiKey: STGSJLZWQHRTGE-UHFFFAOYSA-N

物化性质

• 沸点：
  326.5±22.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932999099
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-甲基-苯并呋喃-2-羧酸 在 sodium amalgam 作用下， 以 sodium hydroxide 为溶剂， 反应 2.5h， 生成 6-甲基-2,3-二氢-苯并呋喃-2-羧酸
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003
• 作为产物：
  描述：

  7-甲基香豆素 生成 6-甲基-苯并呋喃-2-羧酸
  参考文献：
  名称：

  Stoermer, Justus Liebigs Annalen der Chemie, 1900, vol. 312, p. 289

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site
  作者：Yu-Ying Shao、Yong Yin、Bao-Ping Lian、Jia-Fu Leng、Yuan-Zheng Xia、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2020.112105

  日期：2020.3

  with the IC50 value of 0.18 μM against HT29 cells, which was significantly better than that of the reference drugs shikonin and CA-4. What's more, 6c could inhibit tubulin polymerization and compete with [3H] colchicine in binding to tubulin. Further biological studies depicted that 6c can induce cell apoptosis and cell mitochondria depolarize, regulate the expression of apoptosis related proteins in

  设计并合成了一系列新的紫草素-苯并[b]呋喃衍生物作为微管蛋白聚合抑制剂，并对其生物学活性进行了评估。大多数化合物显示出与紫草素相当的抗癌细胞增殖活性，同时对非癌细胞具有较低的细胞毒性。其中，化合物6c对HT29细胞显示出强大的抗癌活性，IC50值为0.18μM，显着优于参考药物紫草素和CA-4。而且，6c可以抑制微管蛋白聚合，并与[3H]秋水仙碱竞争与微管蛋白的结合。进一步的生物学研究表明6c可以诱导细胞凋亡并使细胞线粒体去极化，调节HT29细胞中凋亡相关蛋白的表达。除了，6c激活了HT29细胞在G2 / M期的细胞周期停滞，并影响了细胞周期相关蛋白的表达。此外，6c显示出对细胞迁移和管形成的有效抑制，这有助于抗血管生成。这些结果促使我们将6c视为潜在的微管蛋白聚合抑制剂，值得进一步研究。
• Catalytic Asymmetric Dearomatization by Visible‐Light‐Activated [2+2] Photocycloaddition
  作者：Naifu Hu、Hoimin Jung、Yu Zheng、Juhyeong Lee、Lilu Zhang、Zakir Ullah、Xiulan Xie、Klaus Harms、Mu‐Hyun Baik、Eric Meggers

  DOI：10.1002/anie.201802891

  日期：2018.5.22

  the catalytic asymmetric dearomatization by visible‐light‐activated [2+2] photocycloaddition with benzofurans and one example of a benzothiophene is reported, thereby providing chiral tricyclic structures with up to four stereocenters including quaternary stereocenters. The benzofurans and the benzothiophene are functionalized at the 2‐position with a chelating N‐acylpyrazole moiety which permits the

  报道了一种通过可见光活化的[2 + 2]光环加成与苯并呋喃和一个苯并噻吩实例进行催化不对称脱芳香化反应的新方法，从而提供了具有四个立体中心（包括四级立体中心）的手性三环结构。苯并呋喃和苯并噻吩在2位被N-酰基吡唑螯合部分官能化，从而允许可见光活化的手性铑路易斯手性酸催化剂的配位。计算分子模型揭示了异常区域选择性的起源，并确定了杂环中的杂原子是区域控制的关键。
• [EN] POLYCYCLIC HERG ACTIVATORS<br/>[FR] ACTIVATEURS POLYCYCLIQUES DES CANAUX HERG
  申请人：NOVARTIS AG

  公开号：WO2015161052A1

  公开（公告）日：2015-10-22

  The present invention provides a compound of formula I, in which R1, R2, X and R3 are defined in the Summary of the Invention, or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种I式化合物，其中R1、R2、X和R3在发明摘要中有定义，或其药学上可接受的盐；一种制造本发明化合物的方法，以及其治疗用途。本发明还提供了一种药理活性剂的组合和药物组成。
• Modulation on C- and N-Terminal Moieties of a Series of Potent and Selective Linear Tachykinin NK₂Receptor Antagonists
  作者：Martina Gensini、Maria Altamura、Tula Dimoulas、Valentina Fedi、Danilo Giannotti、Sandro Giuliani、Antonio Guidi、Nicholas J. S. Harmat、Stefania Meini、Rossano Nannicini、Franco Pasqui、Manuela Tramontana、Antonio Triolo、Carlo Alberto Maggi

  DOI：10.1002/cmdc.200900389

  日期：2010.1.4

  Herein we describe the synthesis of a series of new potent tachykinin NK2 receptor antagonists by the modulation of the C‐ and N‐terminal moieties of ibodutant (MEN 15596, 1). The N‐terminal benzo[b]thiophene ring was replaced by different substituted naphthalenes and benzofurans, while further modifications were evaluated at the C‐terminal tetrahydropyran moiety. Most compounds demonstrated a high affinity

  本文中，我们描述了一系列新的有效速激肽NK的合成2通过ibodutant的C-和N-末端部分的调制（MEN 15596，受体拮抗剂1）。N末端的苯并[ b ]噻吩环被不同的取代萘和苯并呋喃取代，同时在C末端的四氢吡喃部分评估了进一步的修饰。大多数化合物表现出对人NK 2受体的高亲和力和体外拮抗剂的高效力，表明可以在分子的两个末端引入广泛的取代基，而不会影响与NK 2受体的相互作用。对选定的化合物进行了体内测试，证实了其作为NK的活性2个拮抗剂。特别是，对豚鼠静脉内和静脉内给药后，化合物61b能够拮抗NK 2诱导的结肠收缩，其作用力和作用持续时间与参考化合物1（MEN 15596，ibodutant）完全相同。
• [EN] GEMINAL SUBSTITUTED QUINUCLIDINE AMIDE COMPOUNDS AS AGONISTS OF ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] COMPOSÉS AMIDE DE QUINUCLIDINE À SUBSTITUANTS GÉMINAL, EN TANT QU'AGONISTES DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE Α7
  申请人：FORUM PHARMACEUTICALS INC

  公开号：WO2016100184A1

  公开（公告）日：2016-06-23

  The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7- nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

  本发明涉及新型的伏立康定酰胺化合物，以及相应的药物组合物，其适用于作为α7-nAChR的激动剂或部分激动剂，并且涉及制备这些化合物和组合物的方法，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物，特别是将该化合物或组合物用于需要的患者的给药方法，例如患有认知缺陷和/或希望增强认知功能的患者，这些患者可能从中获益。