2-bromo-1-(5-nitro-1-benzofuran-2-yl)ethanone | 39904-94-4

• 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: 2-bromo-1-(5-nitro-1-benzofuran-2-yl)ethanone
• 英文别名: 2-bromo-1-(5-nitrobenzofuran-2-yl)ethanone
• CAS: 39904-94-4
• 化学式: C₁₀H₆BrNO₄
• 分子量: 284.066
• InChiKey: IBVWCUZLQQAIGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(5-nitro-1-benzofuran-2-yl)ethanone 在 novozyme 435 、 18-冠醚-6 作用下， 以 乙醇 为溶剂， 生成 (1R)-1-acetoxy-1-(5-nitrobenzofuran-2-yl)ethane
  参考文献：
  名称：

  Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

  摘要：

  Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee]. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00222-2
• 作为产物：
  描述：

  2-乙酰基-5-硝基苯并[b]呋喃 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以73%的产率得到2-bromo-1-(5-nitro-1-benzofuran-2-yl)ethanone
  参考文献：
  名称：

  化学酶法制备羟甲基酮

  摘要：

  一系列的 羟甲基 酮类 4a–g是从相应的卤代甲基获得的酮类 2a–g通过转化为乙酰氧基甲基酮类 图3a-克由18冠6 NaOAc催化的取代反应，随后由Novozyme 435™催化 乙醇分解。这种方便的化学酶促途径为甲基酮1a–g的直接α-羟基化提供了温和，不含重金属的替代方法。

  DOI：

  10.1039/b206851f

文献信息

• Synthesis and bioactivity of novel C2-glycosyl benzofuranylthiazoles derivatives as acetylcholinesterase inhibitors
  作者：Lei Wang、Yu-Ran Wu、Shu-Ting Ren、Long Yin、You-Xian Wang、Shu-Hao Liu、Wei-Wei Liu、Da-Hua Shi、Zhi-Ling Cao、Hui-Min Sun

  DOI：10.1177/1747519819856973

  日期：2019.7

  A new series of C2-glycosyl benzofuranylthiazole derivatives was synthesised by the further cyclization of glycosyl thiourea and 2-(bromoacetyl)-benzofuran via Hantzsch’s method. The corresponding 2-(bromoacetyl)-benzofuran derivatives were obtained by the reaction from various salicylaldehydes, and the glycosyl thiourea was prepared through a series of steps from D-Glucosamine. The acetylcholinesterase-inhibitory

  通过Hantzsch法进一步环化糖基硫脲和2-(溴乙酰基)-苯并呋喃，合成了一系列新的C2-糖基苯并呋喃基噻唑衍生物。由各种水杨醛反应得到相应的2-(溴乙酰基)-苯并呋喃衍生物，由D-氨基葡萄糖通过一系列步骤制备糖基硫脲。产品的乙酰胆碱酯酶抑制活性通过 Ellman 方法测试。随后评估了最具活性的化合物的 50% 抑制浓度值。N-(1,3,4,6-四-O-苄基-2-脱氧-β-D-吡喃葡萄糖基)-4-(5-甲氧基-苯并呋喃-2-基)-1,3-噻唑-2-胺具有最佳的乙酰胆碱酯酶抑制活性，50% 抑制浓度为 2.03 ± 0.26 μM。
• Chemo-enzymatic preparation of hydroxymethyl ketones
  作者：Csaba Paizs、Monica Toşa、Cornelia Majdik、Viktória Bódai、Lajos Novák、Florin-Dan Irimie、László Poppe

  DOI：10.1039/b206851f

  日期：——

  A series of hydroxymethyl ketones 4a–g were obtained from the corresponding halogenomethyl ketones 2a–gvia their transformation into acetoxymethyl ketones 3a–g by 18-crown-6 catalysed substitution with NaOAc followed by Novozyme 435™ catalysed ethanolysis. This convenient chemo-enzymatic route provides a mild, heavy-metal-free alternative to the direct α-hydroxylations of methyl ketones 1a–g.

  一系列的 羟甲基 酮类 4a–g是从相应的卤代甲基获得的酮类 2a–g通过转化为乙酰氧基甲基酮类 图3a-克由18冠6 NaOAc催化的取代反应，随后由Novozyme 435™催化 乙醇分解。这种方便的化学酶促途径为甲基酮1a–g的直接α-羟基化提供了温和，不含重金属的替代方法。
• Potential of aryl–urea–benzofuranylthiazoles hybrids as multitasking agents in Alzheimer's disease
  作者：Belma Zengin Kurt、Isil Gazioglu、Livia Basile、Fatih Sonmez、Tiziana Ginex、Mustafa Kucukislamoglu、Salvatore Guccione

  DOI：10.1016/j.ejmech.2015.07.005

  日期：2015.9

  New benzofuranylthiazole derivatives containing the aryl urea moiety were synthesized and evaluated in vitro as dual acetylcholinesterase (AChE)-butyrylcholinesterase (BuChE) inhibitors. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were assayed. The result showed that all the synthesized compounds exhibited inhibitory activity on both AChE and BuChE with 1-(4-(5-bromobenzofuran-2-yl)thiazol-2-yl)-3-(2fluorophenyl)urea (e25, IC50 value of 3.85 mu M) and 1-(4-iodophenyl)-3-(4-(5-nitrobenzofuran-2-yl) thiazol-2-yl)urea (e38, IC50 value of 2.03 mu M) as the strongest inhibitors against AChE and BuChE, respectively. Compound e38 was 8.5-fold more potent than galanthamine. The selectivity index of e25 and e38 was 2.40 and 0.37 against AChE and BuChE, respectively. Compound e2, e4 and ell (IC50 = 0.2, 0.5 and 1.13 mu M, respectively) showed a better ABTS cation radical scavenging ability than the standard quercetin (IC50 = 1.18 AM). Best poses of compounds e38 on BuChE and e25 on AChE indicate that the thiazole ring and the amidic moiety are important sites of interaction with both ChEs. In addition, the benzofuran ring and phenyl ring are anchored to the side chains of both enzymes by pi-pi(pi-pi) interactions. (C) 2015 Elsevier Masson SAS. All rights reserved.
• [EN] MODULATORS OF PROTEIN KINASES<br/>[FR] MODULATEURS DE PROTÉINES KINASES
  申请人：[en]VIBLIOME THERAPEUTICS, LLC

  公开号：WO2023283369A1

  公开（公告）日：2023-01-12

  Provided herein are small molecule protein kinase modulators, pharmaceutical compositions comprising such, and their uses in treating one or more conditions.
• Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives
  作者：L. Cao、K. Jiang、Zh. Shao、Y. Wang、Sh. Liu、X. Lu、Y. Wu、Ch. Chen、Z. Su、L. Wang、W. Liu、D. Shi、Zh. Cao

  DOI：10.1134/s1070428021090190

  日期：2021.9