4-fluoro-N-(prop-2-ynyl)benzenesulfonamide | 321707-24-8

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-N-(prop-2-ynyl)benzenesulfonamide
• 英文别名: 4-fluoro-N-(prop-2-yn-1-yl)benzenesulfonamide；4-fluoro-N-(2-propynyl)benzenesulfonamide；4-Fluoro-N-(prop-2-yn-1-yl)benzene-1-sulfonamide；4-fluoro-N-prop-2-ynylbenzenesulfonamide
• CAS: 321707-24-8
• 化学式: C₉H₈FNO₂S
• mdl: MFCD02556191
• 分子量: 213.232
• InChiKey: PJMHGJVWZFNTGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-fluoro-N-(prop-2-ynyl)benzenesulfonamide 在 N-iodomorpholine 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Structure optimization and bioactivity evaluation of ThDP analogs targeting cyanobacterial pyruvate dehydrogenase E1

  摘要：

  Harmful cyanobacteria bloom (HCB) has occurred frequently in recent years and it is urgent to develop novel algicides to deal with this problem. In this paper, a series of novel thiamin diphosphate (ThDP) analogs 5a-5g were designed and synthesized targeting cyanobacterial pyruvate dehydrogenase complex E1 (Cy-PDHc E1). Our results showed that compounds 5a-5g have higher inhibitory activities against Cy-PDHc E1 (IC50 9.56-3.48 mu M) and higher inhibitory activities against two model cyanobacteria strains Synechocystis sp PCC6803 (EC50 2.03-1.58 mu M) and Microcystis aeruginosa FACHB905 (EC50 1.86-0.95 mu M). Especially, compound 5b displayed highest inhibitory activities (IC50 = 3.48 mu M) against Cy-PDHc E1 and powerful inhibitory activities against cyanobacteria Synechocystis sp PCC6803 (EC50 = 1.58 mu M) and Microcystis aeruginosa FACHB905 (EC50 = 1.04 mu M). Moreover, the inhibitory activities of compound 5b were even higher than those of copper sulfate (EC50 = 2.02 and 1.71 mu M separately) which has been widely used as algicide against cyanobacteria PCC6803 and FACHB905. The more important was that compound 5b display much higher inhibitory selectivity between Cy-PDHc E1 (Inhibitory rate 97.4%) and porcine PDHc E1 (Inhibitory rate 11.8%) under the same concentration (100 mu M). The inhibition kinetic experiment and molecular docking research showed that compound 5b can inhibit Cy-PDHc E1 by occupying the ThDP-binding pocket and then blocking Cy-PDHc E1 bound to ThDP as competitive inhibitor. The imagines of SEM and TEM showed that cellular microstructures were heavily destroyed under compound 5b stress. Our results demonstrated compound 5b could be taken as a potential lead compound targeting Cy-PDHc E1 to obtain environment-friendly algicide for harmful cyanobacterial blooms control.

  DOI：

  10.1016/j.bmc.2019.115159
• 作为产物：
  描述：

  4-氟苯磺酰氯 、 炔丙胺 在 吡啶 作用下， 反应 20.0h， 以73%的产率得到4-fluoro-N-(prop-2-ynyl)benzenesulfonamide
  参考文献：
  名称：

  新型4-取代的1,2,3-三唑-香豆素杂种的合成，体外抗癌和抗菌活性以及计算机模拟研究

  摘要：

  设计香豆素杂种（在4-取代的1,2,3-三唑芯4 - 35）在微波辐射下具有不同的物理化学性质是由环境友好的铜引入（I）催化的Huisgen 1,3-偶极环加成。香豆素–1,2,3-三唑–苯并稠合杂环杂化物作为一类具有最高抗增殖活性的化合物出现。亲脂性和抗增殖活性之间存在很强的关系，表明亲脂性1,2,3-三唑-香豆素杂物含有苯乙基（13），3,5-二氟苯基（14），5-碘吲哚（30）和苯并咪唑（33和35））亚基显示出最有效的细胞抑制作用。7-甲基香豆素–1,2,3-三唑–2-甲基苯并咪唑杂种33可以突出显示，它对肝细胞癌HepG2细胞具有最高的细胞毒性，IC 50值为0.9μM，选择性高（SI = 50）。该化合物诱导细胞死亡，主要是由于早期凋亡。33的强抗增殖作用可能与其对5-脂氧合酶（5-LO）的抑制作用以及通过干扰细胞内酸性神经酰胺酶（ASAH）的活性扰动鞘脂信号传导有关。对于抗菌

  DOI：

  10.1016/j.ejmech.2016.08.062

文献信息

• [EN] TRICYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES A BASE DE TYRAZOLES TRICYCLIQUES
  申请人：ABBOTT LAB

  公开号：WO2005095387A1

  公开（公告）日：2005-10-13

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物对抑制蛋白酪氨酸激酶具有用处。还公开了制备这些化合物的方法、含有这些化合物的组合物以及使用这些化合物进行治疗的方法。
• Identification of dual role of piperazine-linked phenyl cyclopropyl methanone as positive allosteric modulator of 5-HT2C and negative allosteric modulator of 5-HT2B receptors
  作者：Kartikey Singh、Chandan Sona、Vikash Ojha、Maninder Singh、Ankita Mishra、Ajeet Kumar、Mohammad Imran Siddiqi、Rama P. Tripathi、Prem N. Yadav

  DOI：10.1016/j.ejmech.2018.12.070

  日期：2019.2

  discovery. Recent studies have shown that allosteric modulation of serotonin 2C receptor (5-HT2C) as a viable strategy for the treatment of various central nervous system (CNS) disorders. Considering the critical role of 5-HT2C in the modulation of appetite, a selective positive allosteric modulator (PAM) of 5-HT2C offers a new opportunity for anti-obesity therapeutic development. In this study, phenyl cyclopropyl-linked

  最近，在药物发现中，G蛋白偶联受体的变构调节剂获得了显着的发展。最近的研究表明，血清素2C受体（5-HT 2C）的变构调节是治疗各种中枢神经系统（CNS）疾病的可行策略。考虑到5-HT的关键作用2C食欲的调节，5-HT的选择性正变构调节剂（PAM）2C提供了抗肥胖治疗发展的新契机。在这项研究中，合成了苯基环丙基连接的N-杂环并在5-HT 2C评估了其激动剂和PAM活性。我们的研究表明，咪唑连接的苯基环丙基甲酮对5-HT均具有PAM活性2C和血清素2B受体（5-HT 2B）。有趣的是，哌嗪连接的苯基环丙基甲酮（58）作为5-HT 2C的PAM有活性（将5-HT的E max增加至139％），并且作为5-HT 2B的负变构调节剂（NAM）有活性（降低EC 50 5-HT 10倍，而不会影响E max）。合成正构激动剂氯酪蛋白对5-HT 2B的作用与化合物58相似。分子对接研究表明，所有活性化合物均与5-HT
• Ruthenium Carbene-Mediated Construction of Strained Allenes via the Enyne Cross-Metathesis/Cyclopropanation of 1,6-Enynes
  作者：Ming Gao、Qiangqiang Gao、Xiangbin Hao、Ying Wu、Qingmin Zhang、Guohua Liu、Rui Liu

  DOI：10.1021/acs.orglett.9b04662

  日期：2020.2.7

  Herein, we report on the unprecedented dimerization of 1,6-enynes using a commercially available ruthenium complex RuCl2(PPh3)3, which results in a series of bicyclo[3.1.0]hexyl allene derivatives in moderate to excellent yields. Mechanistic investigation indicates that the in-situ-generated ruthenium vinylidene undergoes a site-selective metathesis process to provide allenyl ruthenium carbene, which

  在本文中，我们报道了使用可商购的钌络合物RuCl2（PPh3）3进行的1,6-烯炔空前的二聚化，结果以中等至极好的收率得到了一系列双环[3.1.0]己基烯丙烯衍生物。机理研究表明，原位生成的亚乙烯基钌经历了位点选择性复分解过程，以提供烯丙基钌卡宾，该烯基可以通过[2 + 2]环加成/金属消除而被烯炔的悬垂C = C键分子内捕获处理。
• Synthesis and Anti-Proliferative Effects of Mono- and Bis-Purinomimetics Targeting Kinases
  作者：Andrea Bistrović、Anja Harej、Petra Grbčić、Mirela Sedić、Sandra Kraljević Pavelić、Mario Cetina、Silvana Raić-Malić

  DOI：10.3390/ijms18112292

  日期：——

  3-d]pyrimidines 4a-4k, unsymmetrical bis-purine isosteres 5a-5e and symmetrical bis-pyrrolo[2,3-d]pyrimidines 6a and 6b connected via di(1,2,3-triazolyl)phenyl linker were synthesized by click chemistry. Whereas mono- 4g and bis-pseudopurine 5e showed selective inhibitory activities on cervical carcinoma (HeLa) cells, bis-pyrrolo[2,3-d]pyrimidine 6b exhibited potent and selective anti-proliferative effect in the

  通过二（1,2 ,,）连接的一系列单吡咯并[2,3-d]嘧啶4a-4k，不对称双嘌呤等排异构体5a-5e和对称双吡咯并[2,3-d]嘧啶6a和6b。通过点击化学合成3-三唑基）苯基接头。mono-4g和bis-pseudopurine 5e对宫颈癌（HeLa）细胞表现出选择性抑制活性，而bis-pyrrolo [2,3-d]嘧啶6b在纳摩尔浓度范围内对胰腺癌（CFPAC）表现出有效和选择性的抗增殖作用。 -1）细胞。其中，化合物6b诱导CFPAC-1细胞中CDK9（细胞周期蛋白依赖性激酶9）/细胞周期蛋白T1的表达水平显着降低，并伴随c-Raf（快速加速纤维肉瘤）和p38 MAP介导的增殖信号减弱。促分裂原活化蛋白）激酶。
• Antitumor and antiviral activities of 4-substituted 1,2,3-triazolyl-2,3-dibenzyl-L-ascorbic acid derivatives
  作者：Andrijana Meščić Macan、Anja Harej、Ines Cazin、Marko Klobučar、Višnja Stepanić、Krešimir Pavelić、Sandra Kraljević Pavelić、Dominique Schols、Robert Snoeck、Graciela Andrei、Silvana Raić-Malić

  DOI：10.1016/j.ejmech.2019.111739

  日期：2019.12

  3-dibenzyl-l-ascorbic acid derivatives with the hydroxyethylene (8a-8u) and ethylidene linkers (10c-10p) were synthesized and evaluated for their antiproliferative activity against seven malignant tumor cell lines and antiviral activity against a broad range of viruses. Conformationally unrestricted spacer between the lactone and 1,2,3-triazole units in 8a-8u series had a profound effect on antitumor activity. Besides

  合成了两个带有羟基乙烯（8a-8u）和亚乙基连接基（10c-10p）的6-（1,2,3-三唑基）-2,3-二苄基-1-抗坏血酸衍生物，并评估了它们的抗增殖活性对七种恶性肿瘤细胞系具有抗性，对多种病毒具有抗病毒活性。8a-8u系列内酯和1,2,3-三唑单元之间的构象不受限制的间隔基对抗肿瘤活性产生了深远的影响。此外，在1,2,3-三唑的C-4处引入长链导致合成了癸基取代的2,3-二苄基-1-抗坏血酸8m，这说明了其选择性和有效的抗增殖活性。乳腺癌MCF-7细胞的细胞数在nM范围内。进一步的分析表明，化合物8m强烈增强了缺氧诱导转录因子1α（HIF-1α）的表达，并在一定程度上降低了一氧化氮合酶2（NOS2）的表达，表明其在调节HIF-1α信号传导途径中的作用。对甲氧基苯基取代的衍生物10g显示出特定的抗巨细胞病毒（CMV）潜力，而脂族取代的衍生物8l和8m具有最有效的但相对非特异性的抗水痘带状疱疹（VZV）活性。