3-[(2-fluorophenyl)methoxy]benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[(2-fluorophenyl)methoxy]benzaldehyde
• 英文别名: 3-(2-Fluoro-benzyloxy)-benzaldehyde；3-[(2-Fluorobenzyl)oxy]benzaldehyde
• 化学式: C₁₄H₁₁FO₂
• mdl: MFCD01590570
• 分子量: 230.239
• InChiKey: LTELQZWKXZXVDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(2-fluorophenyl)methoxy]benzaldehyde 、 3,4,5-三羟基苯甲酰肼 以 乙醇 为溶剂， 反应 6.0h， 以38.6%的产率得到N'-(3-((2-fluorobenzyl)oxy)benzylidene)-3,4,5-trihydroxybenzohydrazide
  参考文献：
  名称：

  Development of hydroxy-based sphingosine kinase inhibitors and anti-inflammation in dextran sodium sulfate induced colitis in mice

  摘要：

  Sphingosine kinase (SphK)-catalyzed production of sphingosine-1-phosphate (S1P) regulates cell growth, survival and proliferation as well as inflammatory status in animals. In recent study we reported the N'-(3-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide scaffold as a potent SphK inhibitor. As a continuation of these efforts, 51 derivatives were synthesized and evaluated by SphK1/2 inhibitory activities for structure-activity relationship (SAR) study. Among them, 33 was identified as the most potent SphK inhibitor. Potency of 33 was also observed to efficiently decrease SphK1/2 expression in human colorectal cancer cells (HCT116) and significantly inhibit dextran sodium sulfate (DSS)-induced colitis as well as the decreased expression of interleukin (IL)-6 and cyclooxygenase-2 (COX-2) in mouse models. Collectively, 33 was validated as an effective SphK inhibitor, which can be served as anti-inflammatory agent to probably treat inflammatory bowel diseases in human. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.047
• 作为产物：
  描述：

  2-氟溴苄 、 间羟基苯甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 以100%的产率得到3-[(2-fluorophenyl)methoxy]benzaldehyde
  参考文献：
  名称：

  Cyclopentyl Derivatives

  摘要：

  本发明涉及以下通式（I）的新型环戊基衍生物：其中X为亚甲基，氧，硫或NR7基团；R1为直链或支链C1-C8烷基或C3-C8烯基或C3-C8炔基链，可选地取代CF3，苯基，苯氧基或萘基，芳香环可选地取代一个或多个C1-C4烷基，卤素，三氟甲基，羟基或C1-C4烷氧基；R2，R3独立地为氢，C1-C3烷基链，卤素，三氟甲基，羟基或C1-C4烷氧基；R4，R5，R6，R7独立地为氢或C1-C6烷基；以及其药学上可接受的盐，作为钠和/或钙通道调节剂活性，因此在预防，缓解和治愈广泛的病理学中有用，包括但不限于神经，精神，心血管，炎症，眼科，泌尿学，代谢和胃肠疾病，其中上述机制已被描述为发挥病理作用。

  公开号：

  EP1533295A1

文献信息

• Indole derivatives as mcp-1 receptor antagonists
  申请人：——

  公开号：US20030144339A1

  公开（公告）日：2003-07-31

  A compound of formula (I) wherein: R 1 is hydrogen, halo or methoxy; R 2 is hydrogen, halo, methyl, ethyl or methoxy; R 3 is a halo group or a trifluoromethyl group; R 4 is a halo group or a trifluoromethyl group; R 5 is hydrogen or halo; R 6 is hydrogen or halo; provided that when R 5 and R 6 are both hydrogen, and one of R 3 or R 4 is chloro or fluoro, then the other is not chloro or fluoro; or a pharmaceutically acceptable salt or prodrug thereof. These compounds have useful activity for the treatment of inflammatory disease, specifically in antagonising an MCP-1 mediated effect in a warm-blooded animal such as a human being.

  一种化合物的化学式（I），其中：R1为氢、卤素或甲氧基；R2为氢、卤素、甲基、乙基或甲氧基；R3为卤素基团或三氟甲基基团；R4为卤素基团或三氟甲基基团；R5为氢或卤素；R6为氢或卤素；但是当R5和R6都为氢，并且R3或R4中的一个为氯或氟时，则另一个不是氯或氟；或其药用可接受的盐或前药。这些化合物对于治疗炎症性疾病具有有用活性，特别是在拮抗MCP-1介导的效应方面，在温血动物（如人类）中。
• Discovery of novel β-carboline/acylhydrazone hybrids as potent antitumor agents and overcome drug resistance
  作者：Yong Li、Wei Yan、Jianhong Yang、Zhuang Yang、Mengshi Hu、Peng Bai、Minghai Tang、Lijuan Chen

  DOI：10.1016/j.ejmech.2018.05.003

  日期：2018.5

  Twenty-four novel β-carboline/acylhydrazone hybrids were synthesized and evaluated for their in vitro antiproliferative activity. Among them, 12r exhibited the most potent activity, with IC50 values of 1–2 μM against panel of cancer cell lines and retained significant activity in multidrug resistant cancer cells. Treated cells were not arrested in any phase of cell cycle but resulted in late cellular

  合成了二十四个新型β-咔啉/酰基ac杂化物，并对其体外抗增殖活性进行了评估。其中，12r表现出最强的活性，对癌细胞系的IC 50值为1-2μM，并且在具有多重耐药性的癌细胞中保留了显着的活性。处理过的细胞在细胞周期的任何阶段都没有停滞，而是导致了MCF-7和MCF-7 / ADR癌细胞的晚期细胞凋亡。重要的是，12r在抑制肿瘤生长方面显示出一定的抗肿瘤作用，且毒性低，副作用小且体重没有明显减轻。
• [EN] MODULATORS OF ION CHANNEL RECEPTORS AND USES THEREOF<br/>[FR] MODULATEURS DE RÉCEPTEURS DE CANAUX IONIQUES ET LEURS UTILISATIONS
  申请人：BIONOMICS LTD

  公开号：WO2019218025A1

  公开（公告）日：2019-11-21

  The present invention relates to compounds useful in the modulation of ion channel activity in cells. The invention also relates to use of these compounds in the treatment of pain, and pharmaceutical compositions containing these compounds and methods for their preparation.

  本发明涉及在细胞中调节离子通道活性的有用化合物。本发明还涉及使用这些化合物治疗疼痛，以及含有这些化合物的制药组合物和其制备方法。
• Cyclopentyl Derivatives
  申请人：Newron Pharmaceuticals S.p.A.

  公开号：EP1533295A1

  公开（公告）日：2005-05-25

  This invention is related to novel cyclopentyl derivatives of the following general formula (I)    wherein Xis methylene, oxygen, sulphur or a NR7 group; R1is a straight or branched C1-C8 alkyl or C3-C8 alkenylene or C3-C8 alkynylene chain, optionally substituted with CF3, phenyl, phenoxy or naphthyl, the aromatic rings optionally substituted by one or more C1-C4 alkyl, halogens, trifluoromethyl, hydroxy or C1-C4 alkoxy groups; R2, R3are independently hydrogen, a C1-C3 alkyl chain,halogen, trifluoromethyl, hydroxy or C1-C4 alkoxy groups; R4, R5, R6, R7are independently hydrogen or C1-C6 alkyl;    and the pharmaceutically acceptable salts thereof that are active as sodium and/or calcium channel modulators and therefore useful in preventing, alleviating and curing a wide range of pathologies, including, but not limited to, neurological, psychiatric, cardiovascular, inflammatory, ophthalmic, urologic, metabolic and gastrointestinal diseases, where the above mechanisms have been described as playing a pathological role.

  本发明涉及以下通式（I）的新型环戊基衍生物：其中X为亚甲基，氧，硫或NR7基团；R1为直链或支链C1-C8烷基或C3-C8烯基或C3-C8炔基链，可选地取代CF3，苯基，苯氧基或萘基，芳香环可选地取代一个或多个C1-C4烷基，卤素，三氟甲基，羟基或C1-C4烷氧基；R2，R3独立地为氢，C1-C3烷基链，卤素，三氟甲基，羟基或C1-C4烷氧基；R4，R5，R6，R7独立地为氢或C1-C6烷基；以及其药学上可接受的盐，作为钠和/或钙通道调节剂活性，因此在预防，缓解和治愈广泛的病理学中有用，包括但不限于神经，精神，心血管，炎症，眼科，泌尿学，代谢和胃肠疾病，其中上述机制已被描述为发挥病理作用。
• Cyclopentyl derivatives
  申请人：Melloni Piero

  公开号：US20070066688A1

  公开（公告）日：2007-03-22

  This invention is related to novel cyclopentyl derivatives of the following general Formula (I), wherein X is methylene, oxygen, sulphur or a NR 7 group; R 1 is a straight or branched C 1 -C 8 alkyl or C 3 -C 8 alkenylene or C 3 -C 8 alkynylene chain, optionally substituted with CF 3 , phenyl, phenoxy or naphthyl, the aromatic rings optionally substituted by one or more C 1 -C 4 alkyl, halogens, trifluoromethyl, hydroxy or C 1 - C4 alkoxy groups; R 2 , R 3 are independently hydrogen, a C 1 -C 3 alkyl chain, halogen, trifluoromethyl, hydroxy or C 1 -C 4 alkoxy groups; R 4 , R 5 , R 6 , R 7 are independently hydrogen or C 1 -C 6 alkyl; and the pharmaceutically acceptable salts thereof that are active as sodium and/or calcium channel modulators and therefor useful in preventing, alleviating and curing a wide range of pathologies, including, but not limited to, neurological, psychiatric, cardiovascular, inflammatory, ophthalmic, urologic, metabolic and gastrointestinal diseases, where the above mechanisms have been described as playing a pathological role.

  本发明涉及以下通式（I）的新型环戊基衍生物，其中X为亚甲基，氧，硫或NR7基团；R1为直链或支链C1-C8烷基或C3-C8烯基或C3-C8炔基链，可选用CF3，苯基，苯氧基或萘基进行取代，芳香环可选用一个或多个C1-C4烷基，卤素，三氟甲基，羟基或C1-C4烷氧基进行取代；R2，R3独立地为氢，C1-C3烷基链，卤素，三氟甲基，羟基或C1-C4烷氧基；R4，R5，R6，R7独立地为氢或C1-C6烷基；以及其药学上可接受的盐，其作为钠和/或钙通道调节剂具有活性，因此在预防，缓解和治疗广泛的病理学方面有用，包括但不限于神经，精神，心血管，炎症，眼科，泌尿科，代谢和胃肠疾病，其中上述机制已被描述为发挥病理作用。