4-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide | 221101-01-5

• 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-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: 4-nitro-N-(prop-2-yn-1-yl)benzene-1-sulfonamide；4-nitro-N-prop-2-ynylbenzenesulfonamide
• CAS: 221101-01-5
• 化学式: C₉H₈N₂O₄S
• mdl: MFCD02556193
• 分子量: 240.24
• InChiKey: DFVNHZALBAFMST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-nitro-N-(prop-2-yn-1-yl)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：

  对硝基苯磺酰氯 、 炔丙胺 在 吡啶 作用下， 以59%的产率得到4-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Pt（II）催化的羰基炔烃异构化反应合成环状烯丙基乙烯基醚

  摘要：

  使用PtCl 2作为催化剂，将几种炔基环氧化物和一种炔基烯丙醇异构化为环状烯丙基乙烯基醚（3,4-二氢-2 H -1,4-恶嗪）。这些烯丙基乙烯基醚中的三种通过水解转化为2-羟基吗啉衍生物，而两种通过热克莱森重排转化为哌啶衍生物。

  DOI：

  10.1016/j.tet.2009.01.065

文献信息

• Tungsten(0)- and Rhenium(I)-Catalyzed Tandem Cyclization of Acetylenic Dienol Silyl Ethers Based on Geminal Carbo-Functionalization of Alkynes
  作者：Hiroyuki Kusama、Yusuke Karibe、Rie Imai、Yuji Onizawa、Hokuto Yamabe、Nobuharu Iwasawa

  DOI：10.1002/chem.201003019

  日期：2011.4.18

  Tungsten(0)‐ and rhenium(I)‐catalyzed reactions of acetylenic dienol silyl ethers based on the concept of geminal carbo‐functionalization of alkynes are reported. Treatment of 3‐siloxy‐1,3‐diene‐7‐ynes with catalytic amounts of [W(CO)6] or [ReCl(CO)5] under photoirradiation conditions gives synthetically useful bicyclo[3.3.0]octane derivatives in good yields. Extremely high catalytic activity is noted

  报道了基于炔烃双碳官能化概念的炔属二烯醇甲硅烷基醚的钨（0）和rh（I）催化反应。在光辐照条件下用催化量的[W（CO）6 ]或[RECl（CO）5 ]处理3-甲硅烷氧基-1,3-二烯-7-炔烃可合成合成有用的双环[3.3.0]辛烷衍生物产量。noted（I）配合物的催化活性极高。该反应已扩展至在其系链中包含氮原子的底物。在这种情况下，有两种合成上有用的杂环化合物：2-氮杂双环[3.3.0]辛烷衍生物9和单环二氢吡咯10获得具有烯丙基取代基的化合物，并且可以通过使用氮取代基和the（I）催化剂类型的适当组合来选择性地制备任何一种产物。该2-氮杂双环[3.3.0]辛烷衍生物9分别由执行处理N个选择性地得到在存在Ns个衍生物[RECL（CO）4（PPH 3）]，而二氢吡咯衍生物10通过处理而获得ñ  Mbs的衍生物与[RECL（CO）5 ] / AgSbF 6。最后，我们将此双碳官能化技术应
• [EN] BETA-LACTAMASE INHIBITORS<br/>[FR] INHIBITEURS DE BÊTA-LACTAMASES
  申请人：VENATORX PHARMACEUTICALS INC

  公开号：WO2017044828A1

  公开（公告）日：2017-03-16

  Described herein are compounds and compositions that modulate the activity of beta -lactamases. In some embodiments, the compounds described herein inhibit beta-lactamase. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.

  本发明描述了能够调节β-内酰胺酶活性的化合物和组合物。在某些实施例中，本发明所描述的化合物可抑制β-内酰胺酶。在某些实施例中，本发明所描述的化合物可用于治疗细菌感染。
• Exploitation of the Ugi–Joullié Reaction in the Synthesis of Libraries of Drug-Like Bicyclic Hydantoins
  作者：Adam Nelson、James Firth、Rong Zhang、Rémy Morgentin、Rachel Guilleux、Tuomo Kalliokoski、Stuart Warriner、Richard Foster、Stephen Marsden

  DOI：10.1055/s-0034-1378704

  日期：——

  efficient method for the synthesis of drug-like fused bicyclic hydantoins is reported. An Ugi–Joullié reaction/cyclisation sequence was exploited as the key complexity-generating process in which trifluoroacetic acid was employed as synthetic equivalent for chloroformic acid. Exemplar diversification of the bicyclic scaffolds was performed to enable subsequent translation to the synthesis of large small molecule

  摘要 报道了合成药物样稠合双环乙内酰脲的通用且有效的方法。Ugi-Joullié反应/环化序列被用作关键的复杂性生成过程，在该过程中，三氟乙酸被用作氯甲酸的合成等价物。进行了双环支架的典型多样化，以使其能够随后翻译为大分子小分子文库的合成，从而导致生产了> 1000种化合物，从而增加了欧洲铅厂的筛选。 报道了合成药物样稠合双环乙内酰脲的通用且有效的方法。Ugi-Joullié反应/环化序列被用作关键的复杂性生成过程，在该过程中，三氟乙酸被用作氯甲酸的合成等价物。进行了双环支架的典型多样化，以使其能够随后翻译为大分子小分子文库的合成，从而导致生产了> 1000种化合物，从而增加了欧洲铅厂的筛选。
• 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。
• Enantioselective Nickel‐Catalyzed <i>anti</i> ‐Arylmetallative Cyclizations onto Acyclic Ketones
  作者：Harley Green、Stephen P. Argent、Hon Wai Lam

  DOI：10.1002/chem.202100143

  日期：2021.4

  reactions involving nickel‐catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary‐alcohol‐containing products in high enantioselectivities, are described. The reversible E/Z isomerization of the alkenylnickel intermediates enables overall anti‐arylmetallative cyclization to occur. The ring

  描述了多米诺反应，涉及镍催化将（杂）芳基硼酸加成到炔烃上，然后将烯基镍中间体环化到束缚的无环酮上，以高对映选择性产生含手性叔醇的产物。烯基镍中间体的可逆E / Z异构化使得整体反芳基金属化环化发生。该产品的环系是某些二芳基吲哚里西啶生物碱的亚结构。