7-chlorobenzofuran-2-carbaldehyde | 179728-80-4

• 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: 7-chlorobenzofuran-2-carbaldehyde
• 英文别名: 7-Chloro-2-formylbenzo[b]furan；7-chloro-1-benzofuran-2-carbaldehyde
• CAS: 179728-80-4
• 化学式: C₉H₅ClO₂
• 分子量: 180.59
• InChiKey: MQEICYGNSDQCKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chlorobenzofuran-2-carbaldehyde 在 苄基三甲基氢氧化铵 作用下， 以 苯 为溶剂， 反应 25.0h， 生成 3-(7-Chloro-benzofuran-2-yl)-4-nitro-butyric acid ethyl ester
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8
• 作为产物：
  描述：

  3 -氯- 2 -羟基苯 在 lithium aluminium tetrahydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 75.0h， 生成 7-chlorobenzofuran-2-carbaldehyde
  参考文献：
  名称：

  通过催化不对称亨利反应 有效合成手性苯并呋喃基β-氨基醇†

  摘要：

  手性β氨基醇配体小号被发现有效地用于铜（II）催化苯并呋喃-2- carbaldehydes与硝基甲烷，而导致的（形成的不对称Henry反应小号）富集的苯并呋喃基β硝基醇与对映选择性令人满意（高达98％ee）。使用该催化方案，可以在短时间内方便地制备生物活性（S）-苯并呋喃基β-氨基醇。

  DOI：

  10.1039/c6ob02569b

文献信息

• Cytotoxicity of new pyridazin-3(2<i>H</i>)-one derivatives orchestrating oxidative stress in human triple-negative breast cancer (MDA-MB-468)
  作者：Najat Bouchmaa、Reda Ben Mrid、Youness Boukharsa、Mohamed Nhiri、Hassan Ait Mouse、Jamal Taoufik、M'hammed Ansar、Abdelmajid Zyad

  DOI：10.1002/ardp.201800128

  日期：2018.12

  characterized by high morbidity and mortality. In the absence of targeted therapy, only chemotherapy is available in this case of cancer. The current study investigated the antitumor effect of new pyridazin‐3(2H)‐one derivatives on the human TNBC cell line, MD‐MB‐468. The in vitro cytotoxic activities were investigated using the tetrazolium‐based MTT assay. Lipid peroxidation, H2O2 content, and the specific activities

  三阴性乳腺癌（TNBC）是一种复杂且侵袭性强的乳腺癌亚型，其特点是发病率和死亡率都很高。在没有靶向治疗的情况下，对于这种癌症，只有化疗可用。目前的研究调查了新型哒嗪-3(2H)-one 衍生物对人 TNBC 细胞系 MD-MB-468 的抗肿瘤作用。使用基于四唑的 MTT 测定研究了体外细胞毒活性。还测定了脂质过氧化、H2O2 含量和抗氧化酶的比活性。发现两种分子 6f 和 7h 对肿瘤细胞具有选择性高活性，IC50 值分别为 3.12 和 4.9 µM。此外，暴露于 6f 的细胞显示出 H2O2 和脂质过氧化水平的显着增加，伴随着谷胱甘肽还原酶 (GR) 和硫氧还蛋白还原酶 (TrxR) 的酶活性降低。化合物6f的细胞毒性可以通过抑制GR和TrxR活性来提高目前治疗TNBC的疗效。
• HIV-1 protease inhibitors with picomolar potency against PI-resistant HIV-1 by modification of the P1′ substituent
  作者：Joseph L. Duffy、Brian A. Kirk、Nancy J. Kevin、Kevin T. Chapman、William A. Schleif、David B. Olsen、Mark Stahlhut、Carrie A. Rutkowski、Lawrence C. Kuo、Lixia Jin、Jiunn H. Lin、Emilio A. Emini、James R. Tata

  DOI：10.1016/s0960-894x(03)00680-2

  日期：2003.10

  Transposition of the pyridyl nitrogen from the P-3 substituent to the P-1' substituent in HIV-1 protease inhibitors (PI) affords compounds such as 3 with an improved inhibitory profile against multiple P450 isoforms. These compounds also displayed increased potency, with 3 inhibiting viral spread (CIC95) at <8 nM for every strain of PI-resistant HIV-1 tested. The poor to modest bioavailability of these compounds may correlate in part to their aqueous solubility. (C) 2003 Elsevier Ltd. All rights reserved.
• Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction
  作者：Wei Chen、Zhao-Hui Zhou、Hong-Bin Chen

  DOI：10.1039/c6ob02569b

  日期：——

  Chiral β-amino alcohol ligands were found effective for the copper(II)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps

  手性β氨基醇配体小号被发现有效地用于铜（II）催化苯并呋喃-2- carbaldehydes与硝基甲烷，而导致的（形成的不对称Henry反应小号）富集的苯并呋喃基β硝基醇与对映选择性令人满意（高达98％ee）。使用该催化方案，可以在短时间内方便地制备生物活性（S）-苯并呋喃基β-氨基醇。
• 3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies
  作者：M Ansar、S Al Akoum Ebriki、R Mouhoub、P Berthelot、C Vaccher、MP Vaccher、N Flouquet、DH Caignard、P Renard、B Pirard、MC Rettori、G Evrard、F Durant、M Debaert

  DOI：10.1016/0223-5234(96)85165-8

  日期：1996.1

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.