(E)-3-(2-fluoro-4-trifluoromethylphenyl)-propenal | 183801-25-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(2-fluoro-4-trifluoromethylphenyl)-propenal
• 英文别名: 3-(2-Fluoro-4-(trifluoromethyl)phenyl)acrylaldehyde；(E)-3-[2-fluoro-4-(trifluoromethyl)phenyl]prop-2-enal
• CAS: 183801-25-4
• 化学式: C₁₀H₆F₄O
• 分子量: 218.151
• InChiKey: ZGJPLKWECPNDFI-OWOJBTEDSA-N

物化性质

• 沸点：
  238.5±35.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-fluoro-4-trifluoromethylphenyl)-propenal 在 sodium tetrahydroborate 、 三溴化磷 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 (E)-N-(coumaran-5-ylmethyl)-N-methyl-3-(2-fluoro-4-trifluoromethylphenyl)prop-2-en-1-amine hydrochloride
  参考文献：
  名称：

  Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate Staphylococcus aureus Infections in Vivo

  摘要：

  Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.

  DOI：

  10.1021/acs.jmedchem.7b00949
• 作为产物：
  描述：

  2-氟-4-(三氟甲基)苯甲醛 在 manganese(IV) oxide 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.83h， 生成 (E)-3-(2-fluoro-4-trifluoromethylphenyl)-propenal
  参考文献：
  名称：

  Synthesis and Antifungal Activities of R-102557 and Related Dioxane-Triazole Derivatives.

  摘要：

  具有二噁烷环的新型三唑化合物被合成。在酸性条件下，二醇前体10与各种芳香醛11-13缩合，得到了一系列二噁烷-三唑化合物14-16。这些化合物14-16的抗真菌活性通过在小鼠感染模型中对白色念珠菌和曲霉菌的评估进行了体内评价。含有单个或两个双键且侧链上带有吸电子基团的芳环衍生物表现出较高的活性。在这些衍生物中，R-102557（16R：Ar=4-（2,2,3,3-四氟丙氧基）苯基）对白色念珠菌、曲霉菌和隐球菌属表现出极佳的体内活性。在大鼠的初步毒性研究中也显示出高度耐受性。

  DOI：

  10.1248/cpb.48.694

文献信息

• Triazole antifungal agent
  申请人：SANKYO COMPANY LIMITED

  公开号：US20010031778A1

  公开（公告）日：2001-10-18

  A compound having the formula: 1 [wherein Ar 1 represents a phenyl which may be substituted, Ar 2 represents a phenyl which may be substituted or a heterocyclic group which may be substituted, R 0 represents a hydrogen atom or a lower alkyl; R 1 represents a lower alkyl; R 2 to R 5 represent a hydrogen atom or an alkyl which may be substituted with halogen, n represents 0 to 2; p represents 0 or 1; q, r and s represent 0 to 2; A represents a 4 - to 7 -membered carbon ring or a 4 - to 7 -membered heterocyclic group]. The compound of the present invention exhibits excellent antifugal activities.

  一种化合物的化学式为：1 [其中Ar1代表可以被取代的苯基，Ar2代表可以被取代的苯基或者可以被取代的杂环基团，R0代表氢原子或较低的烷基；R1代表较低的烷基；R2到R5代表氢原子或者可以被卤素取代的烷基，n代表0到2；p代表0或1；q、r和s代表0到2；A代表一个4到7个碳原子环或者4到7个碳原子杂环基团]。本发明的化合物展现了优异的抗真菌活性。
• VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS
  申请人：Bo Yunxin Y.

  公开号：US20090264424A1

  公开（公告）日：2009-10-22

  Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  具有一般结构和组成的化合物，用于治疗急性、炎症性和神经病性疼痛、牙痛、普通头痛、偏头痛、群集性头痛、混合型血管性和非血管性综合症、紧张性头痛、一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠病、炎症性眼疾、炎症性或不稳定的膀胱疾病、牛皮癣、具有炎症成分的皮肤疾病、慢性炎症状况、炎症性疼痛和相关的高敏感性和触痛、神经病性疼痛和相关的高敏感性和触痛、糖尿病性神经病疼痛、烧伤后神经病疼痛、交感神经维持的疼痛、去神经化综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸、泌尿、胃肠或血管区域的内脏运动障碍、创伤、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠疾病、胃溃疡、十二指肠溃疡、腹泻、坏死性剂引起的胃病变、毛发生长、血管运动或过敏性鼻炎、支气管疾病或膀胱疾病。
• BENZOHETEROCYCLYL ALKYLAMINE COMPOUND AND USE THEREOF
  申请人：East China University of Science and Technology

  公开号：EP3546454A1

  公开（公告）日：2019-10-02

  Disclosed are benzoheterocyclic alkylamine compounds, or a pharmaceutically acceptable salt thereof, or a stereoisomer thereof, and a preparation method thereof, and use of the same in the manufacture of an antibacterial drug as an inhibitor of staphyloxanthin synthesis in Staphylococcus aureus.

  本发明公开了苯并杂环烷基胺化合物或其药学上可接受的盐或其立体异构体及其制备方法，以及将其用于制造抗菌药物作为金黄色葡萄球菌中短链黄素合成的抑制剂。
• Benzoheterocyclic alkylamine compounds and use thereof
  申请人：EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US10829464B2

  公开（公告）日：2020-11-10

  Disclosed are benzoheterocyclic alkylamine compounds, or a pharmaceutically acceptable salt thereof, or a stereoisomer thereof, and a preparation method thereof, and use of the same in the manufacture of an antibacterial drug as an inhibitor of staphyloxanthin synthesis in Staphylococcus aureus.

  公开了苯杂环烷基胺化合物，或者其药学上可接受的盐，或者其立体异构体，以及其制备方法，以及其在制备一种抗菌药物中的用途，作为抑制金黄色葡萄球菌中黄酮生成的抑制剂。
• Novel Staphyloxanthin Inhibitors with Improved Potency against Multidrug Resistant <i>Staphylococcus aureus</i>
  作者：Shuaishuai Ni、Baoli Li、Feifei Chen、Hanwen Wei、Fei Mao、Yifu Liu、Yixiang Xu、Xiaoxi Qiu、Xiaokang Li、Wenwen Liu、Linghao Hu、Dazheng Ling、Manjiong Wang、Xinyu Zheng、Jin Zhu、Lefu Lan、Jian Li

  DOI：10.1021/acsmedchemlett.7b00501

  日期：2018.3.8

  Diapophytoene desaturase (CrtN) is a potential novel target for intervening in the biosynthesis of the virulence factor staphyloxanthin. In this study, 38 1,4-benzodioxan-derived CrtN inhibitors were designed and synthesized to overwhelm the defects of leading compound 4a. Derivative 47 displayed superior pigment inhibitory activity, better hERG inhibitory properties and water solubility, and significantly sensitized MRSA strains to immune clearance in vitro. Notably, 47 displayed excellent efficacy against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate MRSA, VISA), and NRS271 (linezolid-resistant MRSA, LRSA) comparable to that of linezolid and vancomycin in vivo.