4-bromo-2-methylbenzofuran | 219739-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-bromo-2-methylbenzofuran
• 英文别名: 4-bromo-2-methyl-1-benzofuran
• CAS: 219739-70-5
• 化学式: C₉H₇BrO
• mdl: MFCD22039265
• 分子量: 211.058
• InChiKey: HDBQHMPOMJRHBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-2-methylbenzofuran 在 三苯基膦钯 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 dimethyl-[2-(2-methylbenzofuran-4-yl)benzyl]amine hydrochloride
  参考文献：
  名称：

  Substituted 2-dialkylaminoalkylbiphenyl derivatives

  摘要：

  取代的2-二烷基氨基烷基联苯衍生物，其制备方法，包含这些化合物的药物组合物，以及使用这些化合物制备药物和治疗疾病的方法。

  公开号：

  US20020198251A1
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 以0.73 g的产率得到4-bromo-2-methylbenzofuran
  参考文献：
  名称：

  有效合成取代的2-甲基苯并呋喃

  摘要：

  描述了通过在碘存在下可及的烯丙基取代的环己-2-烯酮的芳构化，然后将2-碘甲基-2,3-二氢苯并呋喃中间体脱氢碘化，来有效合成取代的2-甲基苯并呋喃。

  DOI：

  10.1007/s10593-019-02443-3

文献信息

• COMPOUNDS AND METHODS FOR TREATING HIV INFECTIONS
  申请人：YALE UNIVERSITY

  公开号：US20150105351A1

  公开（公告）日：2015-04-16

  The present invention is directed to novel nanomolar and picomolar inhibitors of HIV reverse transcriptase, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV-1 and HIV-2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.

  本发明涉及新型纳摩尔和皮摩尔HIV逆转录酶抑制剂，以及由此制备的药物组合物和用于抑制逆转录酶和治疗HIV感染的方法，特别包括对HIV-1和HIV-2的耐药菌株以及作为HIV感染后果发生的次生疾病状态和/或条件。
• A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products
  作者：Arwel Lewis、Ian Stefanuti、Simon A. Swain、Stephen A. Smith、Richard J. K. Taylor

  DOI：10.1039/b209637b

  日期：2003.12.19

  (-)-apicularen A in 8 steps, this study constitutes a formal total synthesis of (+)-apicularen A. Key steps in the synthetic route include: (i) useful D-glucal elaboration processes, (ii) organometallic displacements at carbohydrate C-6 triflates using Knochel-type and related functionalised, aromatic Grignard reagents, (iii) stereoselective allyltrimethylsilane-acetal reactions generating C-allyl systems

  据报道，从D-葡糖开始的18步合成了针状蛋白前体（-）-6。由于（+）-6已通过8个步骤转变为有效的天然水杨酸酯抗癌剂（-）-apicularen A，因此本研究构成了（+）-apicularen A的正式总合成。合成途径包括：（i）有用的D-葡糖精制工艺，（ii）使用Knochel型和相关功能化芳族格氏试剂在碳水化合物C-6三氟甲磺酸酯上的有机金属置换，（iii）生成C-烯丙基系统的立体选择性烯丙基三甲基硅烷-乙缩醛反应；（iv）来自底物和试剂的立体控制醛烯丙基化过程，以及（v）新型Keck型大内酯化。此外，
• Compounds and methods for treating HIV infections
  申请人：YALE UNIVERSITY

  公开号：US09382245B2

  公开（公告）日：2016-07-05

  The present invention is directed to novel nanomolar and picomolar inhibitors of HIV reverse transcriptase, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV-1 and HIV-2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.

  本发明涉及新型纳摩尔和皮摩尔级别的HIV反转录酶抑制剂，其制药组合物以及抑制反转录酶和治疗HIV感染的方法，特别包括对HIV-1和HIV-2的耐药菌株和/或作为HIV感染后果的二级疾病状态和/或条件的治疗。
• Design of Drug Efficacy Guided by Free Energy Simulations of the β2‐Adrenoceptor
  作者：Nicolas Panel、Duc Duy Vo、Nour Aldin Kahlous、Harald Hübner、Stephanie Tiedt、Pierre Matricon、Jody Pacalon、Oliver Fleetwood、Stefanie Kampen、Andreas Luttens、Lucie Delemotte、Jan Kihlberg、Peter Gmeiner、Jens Carlsson

  DOI：10.1002/anie.202218959

  日期：——

  G-protein-coupled receptors (GPCRs) are important therapeutic targets and numerous approved drugs act by either stimulating or blocking receptor activation. However, the design of ligands that modulate GPCR signaling is challenging. We demonstrate that molecular simulations of GPCRs can be used to predict ligand efficacy and identify potent β2-adrenoceptor agonists.

  G 蛋白偶联受体 (GPCR) 是重要的治疗靶标，许多已获批准的药物通过刺激或阻断受体激活来发挥作用。然而，调节 GPCR 信号的配体设计具有挑战性。我们证明 GPCR 的分子模拟可用于预测配体功效并鉴定有效的 β 2 -肾上腺素能受体激动剂。
• Picomolar Inhibitors of HIV Reverse Transcriptase Featuring Bicyclic Replacement of a Cyanovinylphenyl Group
  作者：Won-Gil Lee、Ricardo Gallardo-Macias、Kathleen M. Frey、Krasimir A. Spasov、Mariela Bollini、Karen S. Anderson、William L. Jorgensen

  DOI：10.1021/ja408917n

  日期：2013.11.6

  Members of the catechol diether class are highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). The most active compounds yield EC50 values below 0.5 nM in assays using human T-cells infected by wild-type HIV-1. However, these compounds such as rilpivirine, the most recently FDA-approved NNRTI, bear a cyanovinylphenyl (CVP) group. This is an uncommon substructure in drugs that gives reactivity concerns. In the present work, computer simulations were used to design bicyclic replacements for the CVP group. The predicted viability of a 2-cyanoindolizinyl alternative was confirmed experimentally and provided compounds with 0.4 nM activity against the wild-type virus. The compounds also performed well with EC50 values of 10 nM against the challenging HIV-1 variant that contains the Lys103Asn/Tyr181Cys double mutation in the RT enzyme. Indolyl and benzofuranyl analogues were also investigated; the most potent compounds in these cases have EC50 values toward wild-type HIV-1 near 10 nM and high-nanomolar activities toward the double-variant. The structural expectations from the modeling were much enhanced by obtaining an X-ray crystal structure at 2.88 Å resolution for the complex of the parent 2-cyanoindolizine 10b and HIV-1 RT. The aqueous solubilities of the most potent indolizine analogues were also measured to be ~40 μg/mL, which is similar to that for the approved drug efavirenz and ~1000-fold greater than for rilpivirine.