Efficient synthesis of sulfonylguanidines via reaction of tetra-substituted urine with ArSO2NCO

被引：3
作者：
Han, Jianjie [1 ]
Zhou, Rongyan [1 ]
Huang, Chao [1 ]
Zeng, Qingkai [1 ]
Long, Qiumeng [1 ]
Zhang, Qianjun [1 ]
Cong, Hang [1 ]
Zhou, Qingdi [2 ]
Wei, Gang [3 ]
Liu, Mao [1 ]
机构：
[1] Guizhou Univ, Coll Chem & Chem Engn, Dept Chem, Guiyang 550025, Guizhou, Peoples R China
[2] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
[3] CSIRO Mineral Resources, POB 218, Lindfield, NSW 2070, Australia
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 48期
基金：
中国国家自然科学基金;
关键词：
Sulfonylguanidine; Urine; Sulfonyl isocyanate; Guanidine; PANCREATIC B-CELLS; 3-ALKYLAMINO-4H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES; BIOLOGICAL EVALUATION; CHANNEL OPENERS; ATP; INHIBITORS;
D O I：
10.1016/j.tetlet.2019.151285
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of sulfonylguanidines via reaction of tetra-substituted urines with ArSO2NCO has been developed with good yields, which provides a convenient way for synthesis of sulfonyl group protected guanidine from urine in one step. (C) 2019 Elsevier Ltd. All rights reserved.
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页数：4
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  • [1] Effect on KATP channel activation properties and tissue selectivity of the nature of the substituent in the 7-and the 3-position of 4H-1,2,4-benzothiadiazine 1,1-dioxides
    Boverie, S
    Antoine, MH
    Somers, F
    Becker, B
    Sebille, S
    Ouedraogo, R
    Counerotte, S
    Pirotte, B
    Lebrun, P
    de Tullio, P
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (10) : 3492 - 3503
  • [2] JD-5006 and JD-5037: Peripherally restricted (PR) cannabinoid-1 receptor blockers related to SLV-319 (Ibipinabant) as metabolic disorder therapeutics devoid of CNS liabilities
    Chorvat, Robert J.
    Berbaum, Jennifer
    Seriacki, Kristine
    McElroy, John F.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (19) : 6173 - 6180
  • [3] Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides
    Chow, Shiao Y.
    Odell, Luke R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05) : 2515 - 2522
  • [4] Triphenylphosphonium salts of 1,2,4-benzothiadiazine 1,1-dioxides related to diazoxide targeting mitochondrial ATP-sensitive potassium channels
    Constant-Urban, Celine
    Charif, Mounia
    Goffin, Eric
    Van Heugen, Jean-Claude
    Elmoualij, Benaissa
    Chiap, Patrice
    Mouithys-Mickalad, Ange
    Serteyn, Didier
    Lebrun, Philippe
    Pirotte, Bernard
    De Tullio, Pascal
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (21) : 5878 - 5881
  • [5] Metal-free C(sp2)-H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination
    Das, Ranajit
    Banerjee, Mainak
    Rai, Rakesh Kumar
    Karri, Ramesh
    Roy, Gouriprasanna
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) : 4243 - 4260
  • [6] 3-Alkylamino-4H-1,2,4-benzothiadiazine 1,1-dioxides as ATP-sensitive potassium channel openers:: Effect of 6,7-disubstitution on potency and tissue selectivity
    de Tullio, P
    Boverie, S
    Becker, B
    Antoine, MH
    Nguyen, QA
    Francotte, P
    Counerotte, S
    Sebille, S
    Pirotte, B
    Lebrun, P
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) : 4990 - 5000
  • [7] Toward tissue-selective pancreatic B-cells KATP channel openers belonging to 3-alkylamino-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides
    de Tullio, P
    Becker, B
    Boverie, S
    Dabrowski, M
    Wahl, P
    Antoine, MH
    Somers, F
    Sebille, S
    Ouedraogo, R
    Hansen, JB
    Lebrun, P
    Pirotte, B
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) : 3342 - 3353
  • [8] Discovery and labeling of high-affinity 3,4-diarylpyrazolines as candidate radioligands for in vivo imaging of cannabinoid subtype-1 (CB1) receptors
    Donohue, Sean R.
    Pike, Victor W.
    Finnema, Sjoerd J.
    Truong, Phong
    Andersson, Jan
    Gulyas, Balazs
    Halldin, Christer
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (18) : 5608 - 5616
  • [9] Synthesis of N-Sulfonyl Arylaldimines Developed by Retesting an Old Process
    Huang, Dayun
    Wang, Xuesong
    Wang, Xingyong
    Chen, Wenwen
    Wang, Xinyan
    Hu, Yuefei
    [J]. ORGANIC LETTERS, 2016, 18 (03) : 604 - 607
  • [10] Synthesis of 13C6-labeled, dual-target inhibitor of cannabinoid-1 receptor (CB1R) and inducible nitric oxide synthase (iNOS)
    Iyer, Malliga R.
    Cinar, Resat
    Coffey, Nathan J.
    Kunos, George
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2018, 61 (10) : 773 - 779
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