3-(2-苯并呋喃)苯甲酸 | 835595-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 3-(2-苯并呋喃)苯甲酸
• 英文名称: 3-(benzofuran-2-yl)benzoic acid
• 英文别名: 3-(2-benzofuranyl)benzoic acid；3-(1-benzofuran-2-yl)benzoic acid
• CAS: 835595-07-8
• 化学式: C₁₅H₁₀O₃
• mdl: MFCD17677559
• 分子量: 238.243
• InChiKey: YXFVUPBRAAWFRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-苯并呋喃)苯甲酸 在 4-二甲氨基吡啶 、 potassium cyanide 、 羟胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2S,3S)-2-(3-(1-benzofuran-2-yl)benzamido)-N-hydroxy-3-methylpentanamide
  参考文献：
  名称：

  Synthesis and activity of isoleucine sulfonamide derivatives as novel botulinum neurotoxin serotype A light chain inhibitors

  摘要：

  The botulinum neurotoxin (BoNT) is the most lethal protein known to man causing the deadly disease botulinum. The neurotoxin, composed of a heavy (HC) and light (LC) chain, work in concert to cause muscle paralysis. A therapeutic strategy to treat individuals infected with the neurotoxin is inhibiting the catalytic activity of the BoNT LC. We report the synthesis, inhibition study and computational docking analysis of novel small molecule BoNT/A LC inhibitors. A structure activity relationship study resulted in the discovery of D-isoleucine functionalized with a hydroxamic acid on the C-terminal and a biphenyl with chlorine at C- 2 connected by a sulfonamide linker at the N-terminus. This compound has a measured IC50 of 0.587 mu M for the BoNT/A LC. Computational docking analysis indicates the sulfonamide linker adopts a geometry that is advantageous for binding to the BoNT LC active site. In addition, Arg363 is predicted to be involved in key binding interactions with the scaffold in this study.

  DOI：

  10.1016/j.bmc.2020.115659
• 作为产物：
  描述：

  3-溴苯甲酸甲酯 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 24.17h， 生成 3-(2-苯并呋喃)苯甲酸
  参考文献：
  名称：

  Synthesis and activity of isoleucine sulfonamide derivatives as novel botulinum neurotoxin serotype A light chain inhibitors

  摘要：

  The botulinum neurotoxin (BoNT) is the most lethal protein known to man causing the deadly disease botulinum. The neurotoxin, composed of a heavy (HC) and light (LC) chain, work in concert to cause muscle paralysis. A therapeutic strategy to treat individuals infected with the neurotoxin is inhibiting the catalytic activity of the BoNT LC. We report the synthesis, inhibition study and computational docking analysis of novel small molecule BoNT/A LC inhibitors. A structure activity relationship study resulted in the discovery of D-isoleucine functionalized with a hydroxamic acid on the C-terminal and a biphenyl with chlorine at C- 2 connected by a sulfonamide linker at the N-terminus. This compound has a measured IC50 of 0.587 mu M for the BoNT/A LC. Computational docking analysis indicates the sulfonamide linker adopts a geometry that is advantageous for binding to the BoNT LC active site. In addition, Arg363 is predicted to be involved in key binding interactions with the scaffold in this study.

  DOI：

  10.1016/j.bmc.2020.115659

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005009993A1

  公开（公告）日：2005-02-03

  Compounds of the formula (I) are disclosed which are large conductance calcium activated potassium channel openers (BK channels openers) and are useful in the treatment of urinary tract disorders: (I), or a pharmaceutically acceptable salt thereof.

  公式（I）的化合物被披露，它们是大导电性钙激活钾通道开放剂（BK通道开放剂），并且在治疗泌尿道疾病方面是有用的：（I），或其药用可接受的盐。
• Novel compounds useful for bradykinin B1 receptor antagonism
  申请人：Ye Michael Xiaocong

  公开号：US20070032475A1

  公开（公告）日：2007-02-08

  Disclosed are compounds that are bradykinin B 1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B 1 receptor.

  揭示了一种化合物，它们是布雷金肽B1受体拮抗剂，可用于治疗或缓解由布雷金肽B1受体介导的哺乳动物疾病，或与疾病状况相关的不良症状。
• Novel compounds
  申请人：Lee Dennis

  公开号：US20060205751A1

  公开（公告）日：2006-09-14

  Compounds of the formula (I) are disclosed which are large conductance calcium activated potassium channel openers (BK channels openers) and are useful in the treatment of urinary tract disorders: or a pharmaceutically acceptable salt thereof.

  公开了式子(I)的化合物，它们是大导电性钙激活钾通道开放剂（BK通道开放剂），并且在治疗泌尿道疾病方面非常有用：或其药学上可接受的盐。
• Acyltryptophanols
  申请人：Wortmann Lars

  公开号：US20070060573A1

  公开（公告）日：2007-03-15

  The present patent application relates to acyltryptophanols of the general formula I, in which Q, X, Y, W, R1, R2, R3, R4, R5, R8 have the meanings stated in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本专利申请涉及一般式I的酰基色氨酸醇，其中Q、X、Y、W、R1、R2、R3、R4、R5、R8具有说明书中所述的含义。本发明的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。
• NOVEL COMPOUNDS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1648885A1

  公开（公告）日：2006-04-26