- Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light
-
An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.
- Fu, Ying,Wu, Qing-Kui,Du, Zhengyin
-
supporting information
p. 1896 - 1900
(2021/04/06)
-
- A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
-
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
- Huang, Binbin,Guo, Lin,Xia, Wujiong
-
supporting information
p. 2095 - 2103
(2021/03/26)
-
- N-Substituted Nipecotic Acids as (S)-SNAP-5114 Analogues with Modified Lipophilic Domains
-
Potential mGAT4 inhibitors derived from the lead substance (S)-SNAP-5114 have been synthesized and characterized for their inhibitory potency. Variations from the parent compound included the substitution of one of its aromatic 4-methoxy and 4-methoxyphenyl groups, respectively, with a more polar moiety, including a carboxylic acid, alcohol, nitrile, carboxamide, sulfonamide, aldehyde or ketone function, or amino acid partial structures. Furthermore, it was investigated how the substitution of more than one of the aromatic 4-methoxy groups affects the potency and selectivity of the resulting compounds. Among the synthesized test substances (S)-1-{2-[(4-formylphenyl)bis(4-methoxyphenyl)-methoxy]ethyl}piperidine-3-carboxylic acid, that features a carbaldehyde function in place of one of the aromatic 4-methoxy moieties of (S)-SNAP-5114, was found to have a pIC50 value of 5.89±0.07, hence constituting a slightly more potent mGAT4 inhibitor than the parent substance while showing comparable subtype selectivity.
- B?ck, Michael C.,H?fner, Georg,Wanner, Klaus T.
-
-
- Controlled synthesis of N, N-dimethylarylsulfonamide derivatives as nematicidal agents
-
Gramine can be intelligently and efficiently supplied with N, N-dimethylamino group and then reacted with the corresponding sulfonyl chlorides to synthesize N, N-dimethylarylsulfonamides. We herein designed and controlled synthesis of N, N-dimethylarylsulfonamide derivatives, and first reported the results of the nematicidal activity of 15 title compounds 3a-o against Meloidogyne incongnita in vitro, respectively. Among all of the title derivatives, compounds 3a, 3c, 3k, and 3o exhibited potent nematicidal activity with median lethal concentration (LC50) values ranging from 0.22 to 0.26 mg/L. Most noteworthy, N, N-dimethyl-4-methoxyphenylsulfonamide (3c) and N, N-dimethyl-8-quinolinesulfonamide (3o) showed the best promising and pronounced nematicidal activity, with LC50 values of 0.2381 and 0.2259 mg/L, respectively.
- Chen, Gen-Qiang,Xia, Yan-Fei,Yang, Jin-Ming,Che, Zhi-Ping,Sun, Di,Li, Shen,Tian, Yue-E,Liu, Sheng-Ming,Jiang, Jia,Lin, Xiao-Min
-
p. 1197 - 1206
(2019/12/03)
-
- HALOALLYLAMINE SULFONE DERIVATIVE INHIBITORS OF LYSYL OXIDASES AND USES THEREOF
-
The present invention relates to novel compounds which are capable of inhibiting certain amine oxidase enzymes. These compounds are useful for treatment of a variety of indications, e.g., fibrosis, cancer and/or angiogenesis in human subjects as well as i
- -
-
Paragraph 0294
(2020/02/23)
-
- Preparation method of N,N-dimethylsulfamide derivatives
-
The invention discloses a preparation method of N,N-dimethylsulfamide derivatives and belongs to the technical field of synthesis of medical compounds. The preparation method comprises the following steps: reacting gramine, a reactant with sulfonyl chloride groups and an alkaline substance with any one of solvents such as CH2Cl2, CH3COCH3 and CH3CN at a temperature of minus 15 DEG C to 80 DEG C for 24-48 hours so as to obtain the product, wherein the molar ratio of the gramine to the reactant to the alkaline substance is (1.0-2.0):(1.2-4.0):(1.5-6.0). The N,N-dimethylsulfamide derivatives can be simply and efficiently prepared withlow cost, and the yield is up to 70-98%.
- -
-
Paragraph 0096-0100; 0170
(2019/10/01)
-
- Charge-Transfer Complex Promoted Regiospecific C?N Bond Cleavage of Vicinal Tertiary Diamines
-
A catalyst-free, charge-transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C?N bond cleavage of vicinal tertiary diamines. (Figure presented.).
- Fu, Ying,Xu, Qin-Shan,Shi, Chun-Zhao,Du, Zhengyin,Xiao, Caiqin
-
supporting information
p. 3502 - 3506
(2018/09/14)
-
- Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides
-
By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.
- Bao, Xiaodong,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Liang, Guang,Xia, Qinqin
-
supporting information
p. 2853 - 2858
(2018/06/25)
-
- One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
-
A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.
- Leas, Derek A.,Dong, Yuxiang,Vennerstrom, Jonathan L.,Stack, Douglas E.
-
supporting information
p. 2518 - 2521
(2017/05/24)
-
- Conformational Aspects in the Design of Inhibitors for Serine Hydroxymethyltransferase (SHMT): Biphenyl, Aryl Sulfonamide, and Aryl Sulfone Motifs
-
Malaria remains a major threat to mankind due to the perpetual emergence of resistance against marketed drugs. Twenty-one pyrazolopyran-based inhibitors bearing terminal biphenyl, aryl sulfonamide, or aryl sulfone motifs were synthesized and tested towards serine hydroxymethyltransferase (SHMT), a key enzyme of the folate cycle. The best ligands inhibited Plasmodium falciparum (Pf) and Arabidopsis thaliana (At) SHMT in target, as well as PfNF54 strains in cell-based assays in the low nanomolar range (18–56 nm). Seven co-crystal structures with P. vivax (Pv) SHMT were solved at 2.2–2.6 ? resolution. We observed an unprecedented influence of the torsion angle of ortho-substituted biphenyl moieties on cell-based efficacy. The peculiar lipophilic character of the sulfonyl moiety was highlighted in the complexes with aryl sulfonamide analogues, which bind in their preferred staggered orientation. The results are discussed within the context of conformational preferences in the ligands.
- Schwertz, Geoffrey,Frei, Michelle S.,Witschel, Matthias C.,Rottmann, Matthias,Leartsakulpanich, Ubolsree,Chitnumsub, Penchit,Jaruwat, Aritsara,Ittarat, Wanwipa,Sch?fer, Anja,Aponte, Raphael A.,Trapp, Nils,Mark, Kerstin,Chaiyen, Pimchai,Diederich, Fran?ois
-
supporting information
p. 14345 - 14357
(2017/10/09)
-
- Copper-mediated S-N formation via an oxygen-activated radical process: A new synthesis method for sulfonamides
-
Copper-mediated direct S-N formation using readily available starting materials via an oxygen-activated radical process has been developed. This method provides a novel and direct approach for synthesis of sulfonamides under air conditions. the Partner Organisations 2014.
- Huang, Xin,Wang, Jichao,Ni, Zhangqin,Wang, Sichang,Pan, Yuanjiang
-
supporting information
p. 4582 - 4584
(2014/05/06)
-
- 2-AZA-BICYCLO[2.2.2]OCTANE COMPOUNDS AND USES THEREOF
-
This invention relates to 2-aza-bicyclo [2.2.2] octane compounds (and salts thereof), the process for making such a compound and pharmaceutical compositions comprising such a compound. The invention also relates to the use of the compounds for modulating
- -
-
Page/Page column 64
(2010/08/09)
-
- Synthesis and PKCθ inhibitory activity of a series of 5-vinyl phenyl sulfonamide-3-pyridinecarbonitriles
-
A series of 5-vinyl phenyl sulfonamide-3-pyridinecarbonitriles were prepared and evaluated as PKCθ inhibitors. Optimization resulted in the identification of compound 15 with an IC50 value 0.44 nM for the inhibition of PKCθ with 150-fold select
- Shim, Jaechul,Eid, Clark,Lee, Julie,Liu, Erica,Chaudhary, Divya,Boschelli, Diane H.
-
scheme or table
p. 6575 - 6577
(2010/06/12)
-
- ARYL SULFONAMIDES USEFUL FOR MODULATION OF THE PROGESTERONE RECEPTOR
-
In one embodiment, compounds of the following structure are described, wherein R1 to R7 are described herein. Also provided are methods for preparing these compounds and methods of contraception; treating or preventing fibroids; trea
- -
-
Page/Page column 8
(2008/12/08)
-
- SPIROPIPERIDINE BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
-
The present invention is directed to spiropiperidine compounds of formula (I) and tautomers thereof, which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as
- -
-
Page/Page column 43
(2008/06/13)
-
- SUBSTITUTED BIPHENYL DERIVATIVE
-
The present invention relates to a biaryl derivative or a pharmacologically acceptable salt thereof having an excellent collagen-synthesis inhibition activity. A biaryl derivative having a structure represented by the following General Formula (I) or a pharmacologically acceptable salt thereof: wherein R1 represents a C6-C10 aryl group which is substituted with one to three group(s) each independently selected from the group consisting of a group defined by formula R-L-, a di-(C1-C6 alkyl)amino group, a di-(C1-C6 alkyl)aminosulfonyl group, a hydroxyaminocarbonyl group, and a halogen atom, and so on; R represents a C1-C6 alkyl group, and so on; L represents a sulfonyl group, an aminosulfonyl group, or a sulfonylamino group, and so on; R2 represents a hydrogen atom, and so on; A represents a group defined by formula (II), (III), or (IV); R3 represents a C1-C6 alkyl group, and so on; and R4 represents a C1-C6 alkyl group, and so on.
- -
-
Page/Page column 108
(2010/11/27)
-
- Acetylenyl-pyrazolo-pyrimidine derivatives
-
The present invention relates to compounds of formula (I): wherein R1 to R3, A, M, L, E, G, and J are as defined in the description and claims. The invention also relates to a process for the manufacture of such compounds, pharmaceutical compositions containing them, and methods for treating CNS disorders.
- -
-
Page/Page column 29
(2008/06/13)
-
- SELECTIVE ESTROGEN RECEPTOR MODULATORS CONTAINING A PHENYLSULFONYL GROUP
-
The present invention relates to a selective estrogen receptor modulator of formula I or a pharmaceutical acid addition salt thereof; useful, e.g., for treating endometriosis and/or uterine leiomyoma/leiomyomata.
- -
-
Page/Page column 60
(2008/06/13)
-
- Remarkably Mild and Simple Preparations of Sulfinates, Sulfonyl Chlorides and Sulfonamides from Thioanisoles
-
New and high yielding procedures to convert thioanisoles into versatile sulfonyl chloride derivatives were developed by strategically taking advantage of the Pummerer reaction.
- De Vleeschauwer, Marc,Gauthier, Jacques Yves
-
p. 375 - 377
(2007/10/03)
-