6-硝基-2,3-二氢-1-苯并呋喃 | 911300-51-1

• 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: 6-硝基-2,3-二氢-1-苯并呋喃
• 英文名称: 6-nitro-2,3-dihydrobenzofuran
• 英文别名: 6-nitro-2,3-dihydro-1-benzofuran
• CAS: 911300-51-1
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: ZIOGUNUUBPDESL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-硝基-2,3-二氢-1-苯并呋喃 在 platinum(IV) oxide 盐酸 、 氢气 、 硝酸 、 溶剂黄146 、 三氟乙酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 100.0 ℃ 、206.85 kPa 条件下， 反应 45.5h， 生成 3-chloro-7,8-dihydrofuro[2,3-g][1,2,4]benzotriazine 1-oxide
  参考文献：
  名称：

  WO2006/104406

  摘要：

  公开号：
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 吡啶 、 盐酸 、 硫酸 、 palladium on activated charcoal 、 氢气 、 硝酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 溶剂黄146 、 三氟乙酸 为溶剂， 反应 24.0h， 生成 6-硝基-2,3-二氢-1-苯并呋喃
  参考文献：
  名称：

  [EN] FUSED RING COMPOUND AS NAV1.8 INHIBITOR AND USE THEREOF
  [FR] COMPOSÉ À CYCLES FUSIONNÉS EN TANT QU'INHIBITEUR DE NAV1.8 ET SON UTILISATION
  [ZH] 作为Nav1.8抑制剂的并环化合物及其用途

  摘要：

  本发明提供一种作为钠通道阻滞剂的并环类化合物及其用途，其对钠离子通道Nav1.8具有抑制活性，可用作广泛疼痛治疗的药物。

  公开号：

  WO2022121805A1
• 作为试剂：
  描述：

  6-硝基-2,3-二氢-1-苯并呋喃-5-基胺 、 硫酸 、 sodium nitrite 、 phosphinic acid 在 乙酸乙酯 、 水 、 Sodium sulfate-III 、 6-硝基-2,3-二氢-1-苯并呋喃 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 以This resulted in 42 g (76%) of 6-nitro-2,3-dihydrobenzofuran as a red yellow solid的产率得到6-硝基-2,3-二氢-1-苯并呋喃
  参考文献：
  名称：

  4' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

  摘要：

  本公开提供了具有亲和力的5-HT6受体的化合物，其化学式为(I)：其中R1、R2、R5、R6、B、D、E、G、Q、x和n如本文所定义。该公开还涉及制备这种化合物的方法、含有这种化合物的组合物以及使用这种化合物的方法。

  公开号：

  US20080318941A1

文献信息

• 6' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
  申请人：Dunn Robert

  公开号：US20080200471A1

  公开（公告）日：2008-08-21

  The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R 1 —R 4 A, B, D, E, and G are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

  本公开提供了具有亲和力的化合物，其对5-HT6受体具有亲和力，其化学式为（I）： 其中R1-R4，A，B，D，E和G如本文所定义。该公开还涉及制备这种化合物的方法，含有这种化合物的组合物，以及这些化合物的使用方法。
• Tricyclic 1,2,4-Triazine Oxides and Compositions for Therapeutic Use in Cancer Treatments
  申请人：Hay Michael Patrick

  公开号：US20090186886A1

  公开（公告）日：2009-07-23

  The invention relates to novel tricyclic 1,2,4-triazine-1-oxides and novel tricyclic 1,2,4-triazine-1,4-dioxides of formula I and to related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及新型三环1,2,4-三嗪-1-氧化物和新型三环1,2,4-三嗪-1,4-二氧化物的公式I以及相关类似物，它们的制备以及它们作为低氧选择性药物和放射增敏剂用于癌症治疗，可以单独使用或与放射线和/或其他抗癌药物联合使用。
• Tricyclic [1,2,4]Triazine 1,4-Dioxides As Hypoxia Selective Cytotoxins
  作者：Michael P. Hay、Kevin O. Hicks、Karin Pchalek、Ho H. Lee、Adrian Blaser、Frederik B. Pruijn、Robert F. Anderson、Sujata S. Shinde、William R. Wilson、William A. Denny

  DOI：10.1021/jm800967h

  日期：2008.11.13

  A series of novel tricyclic triazine-di-N-oxides (TTOs) related to tirapazamine have been designed and prepared. A wide range of structural arrangements with cycloalkyl, oxygen-, and nitrogen-containing Saturated rings fused to the triazine core, coupled with various side chains linked to either hemisphere, resulted in TTO analogues that displayed hypoxia-selective cytotoxicity in vitro. Optimal rates of hypoxic metabolism and tissue diffusion coefficients were achieved with fused cycloalkyl rings in combination with both the 3-aminoalkyl or 3-alkyl substituents linked to weakly basic soluble amines. The selection was further refined 7 using pharmacokinetic/phamacodynamic model predictions of the in vivo hypoxic potency (AUC(req)) and selectivity (HCD) with 12 TTO analogues predicted to be active in Vivo, Subject to the achievement of adequate plasma pharmacokinetics.
• Structure–activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template
  作者：Phuong-Thao Tran、Van-Hai Hoang、Shivaji A. Thorat、Sung Eun Kim、Jihyae Ann、Yu Jin Chang、Dong Woo Nam、Hyundong Song、Inhee Mook-Jung、Jiyoun Lee、Jeewoo Lee

  DOI：10.1016/j.bmc.2013.04.005

  日期：2013.7

  In an effort to design inhibitors of human glutaminyl cyclase (QC), we have synthesized a library of N-aryl N-(5-methyl-1H-imidazol-1-yl)propyl thioureas and investigated the contribution of the aryl region of these compounds to their structure-activity relationships as cyclase inhibitors. Our design was guided by the proposed binding mode of the preferred substrate for the cyclase. In this series, compound 52 was identified as the most potent QC inhibitor with an IC50 value of 58 nM, which was two-fold more potent than the previously reported lead 2. Compound 52 is a most promising candidate for future evaluation to monitor its ability to reduce the formation of pGlu-A beta and A beta plaques in cells and transgenic animals. (C) 2013 Elsevier Ltd. All rights reserved.
• Discovery of dual-acting opioid ligand and TRPV1 antagonists as novel therapeutic agents for pain
  作者：Hobin Lee、Songyeon Ahn、Jihyae Ann、Heejin Ha、Young Dong Yoo、Young Ho Kim、Ji-Young Hwang、Kwang-Hyun Hur、Choon-Gon Jang、Larry V. Pearce、Timothy E. Esch、Nancy E. Lewin、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.ejmech.2019.111634

  日期：2019.11

  In order to discover a novel type of analgesic, we investigated dual activity ligands with TRPV1 antagonism and mu-opioid receptor affinity with the goal of eliciting synergistic analgesia while avoiding the side effects associated with single targeting. Based on a combination approach, a series of 4-benzyl-4-(dimethylamino)piperidinyl analogues were designed, synthesized and evaluated for their receptor activities. Among them, compound 49 exhibited the most promising dual-acting activity toward TRPV1 and the mu-opioid receptor in vitro. In vivo, 49 displayed potent, dose-dependent antinociceptive activity in both the 1st and 2nd phases in the formalin assay. Consistent with its postulated mechanism, we confirmed that in vivo, as in vitro, compound 49 both antagonized TRPV1 and functioned as a mu-opioid agonist. This result indicates that dual-acting TRPV1 antagonist/mu-opioid ligands can be made and represent a new and promising class of analgesic. (C) 2019 Elsevier Masson SAS. All rights reserved.