- Sequential C-S and S-N Coupling Approach to Sulfonamides
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A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
- Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 1841 - 1845
(2020/03/04)
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- Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound
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The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.
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Paragraph 0067-0071
(2019/11/12)
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- Development of novel silanol-based human pregnane X receptor (PXR) agonists with improved receptor selectivity
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Pregnane X receptor (PXR) is a ligand-dependent transcription factor that is considered to be a potential therapeutic target for multiple diseases. Herein, we report the development and structure-activity relationship studies of a new series of hPXR agoni
- Toyama, Hirozumi,Shirakawa, Hitoshi,Komai, Michio,Hashimoto, Yuichi,Fujii, Shinya
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p. 4493 - 4501
(2018/08/06)
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- Altered activity profile of a tertiary silanol analog of multi-targeting nuclear receptor modulator T0901317
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We report the design, synthesis, and physicochemical/biological evaluation of novel silanol derivative 6 (sila-T) as a silanol analog of multi-target nuclear receptor modulator T0901317 (5). Compound 6 showed intermediate hydrophobicity between the corres
- Toyama, Hirozumi,Sato, Shoko,Shirakawa, Hitoshi,Komai, Michio,Hashimoto, Yuichi,Fujii, Shinya
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p. 1817 - 1820
(2016/07/27)
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- Structure-based design of substituted hexafluoroisopropanol- arylsulfonamides as modulators of RORc
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The structure-activity relationships of T0901317 analogs were explored as RORc inverse agonists using the principles of property- and structure-based drug design. An X-ray co-crystal structure of T0901317 and RORc was obtained and provided molecular insight into why T0901317 functioned as an inverse agonist of RORc; whereas, the same ligand functioned as an agonist of FXR, LXR, and PXR. The structural data was also used to design inhibitors with improved RORc biochemical and cellular activities. The improved inhibitors possessed enhanced selectivity profiles (rationalized using the X-ray crystallographic data) against other nuclear receptors.
- Fauber, Benjamin P.,De Leon Boenig, Gladys,Burton, Brenda,Eidenschenk, Celine,Everett, Christine,Gobbi, Alberto,Hymowitz, Sarah G.,Johnson, Adam R.,Liimatta, Marya,Lockey, Peter,Norman, Maxine,Ouyang, Wenjun,Rene, Olivier,Wong, Harvey
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supporting information
p. 6604 - 6609
(2014/01/06)
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- Design, synthesis, and activity evaluation of broad-spectrum small-molecule inhibitors of anti-apoptotic Bcl-2 family proteins: Characteristics of broad-spectrum protein binding and its effects on anti-tumor activity
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On the basis of the comparison of the structure of the Bim BH3: Bcl-x L complex and that of the ABT-737: Bcl-xL complex, a series of class A compounds were designed. These compounds had the basic skeleton of ABT-737 and the h2 residues of Bim BH3. These residues had shown themselves to be relevant to Bim BH3's broad-spectrum binding properties in saturation mutagenesis assays. Unlike ABT-737, which is a selective inhibitor of anti-apoptotic members of the Bcl-2 protein family, the class A compounds showed broad-spectrum binding activity to target proteins similar to those of Bim BH3 peptide. Then class B compounds were synthesized by modifying the structure of the most effective class A compound, A-4. Most of these class B compounds showed better binding affinity to the target proteins than the class A compounds had. They also showed themselves more effective than ABT-737 at inhibiting growth in multiple tumor cell lines known to express Bcl-x L, Bcl-2, and Mcl-1 proteins at high levels. Compounds B-11 and B-12 had the strongest anti-tumor activity of any compounds we produced. This study suggests that it is feasible to design small-molecule inhibitors based on the structure of Bim BH3, which shows broad-spectrum binding to Bcl-xL, Bcl-2, and Mcl-1 proteins. Our results also suggest that the broad-spectrum properties of small-molecule inhibitors binding to target proteins play a critical role in inhibiting the growth of many tumor cells. Finally, our study provides a series of lead compounds that merit further research into anti-cancer therapeutics.
- Zheng, Can-Hui,Yang, Hui,Zhang, Meng,Lu, Shi-Hai,Shi, Duo,Wang, Juan,Chen, Xiu-Hua,Ren, Xiao-Hui,Liu, Jia,Lv, Jia-Guo,Zhu, Ju,Zhou, You-Jun
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scheme or table
p. 39 - 44
(2012/02/16)
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- SULFONAMIDE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
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Compounds are provided according to formula (1), wherein W, X, Z, R1, R2, R3, and ml are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others. Provided compounds and pharmaceutical compositions thereof are also useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example immune-mediated disorders and autoimmune diseases, including multiple sclerosis, type-1 diabetes mellitus, type-2 diabetes mellitus, rheumatoid arthritis, psoriasis, contact dermatitis, obesity, systemic lupus erythematosus, graft-versus host disease, transplant rejection, and others.
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Page/Page column 66
(2010/12/17)
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- Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands
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A highly general, convenient, and inexpensive catalyst system was developed for the N-arylation of sulfonamides with aryl iodides or bromides by using 5-20 mol % of CuI as catalyst, 20 mol % of N-methylglycine (for aryl iodides) or N,N-dimethylglycine (for aryl bromides) as ligand, and K3PO 4 as base.
- Deng, Wei,Liu, Lei,Zhang, Chen,Liu, Min,Guo, Qing-Xiang
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p. 7295 - 7298
(2007/10/03)
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- Benzamidoaldehydes and their use as cysteine protease inhibitors
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Compounds of the formula where R1, R2, R3, X and n are as defined in the description, are inhibitors of cysteine protease.
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- Selective monodesulfonylation of N,N-disulfonylarylamines with tetrabutylammonium fluoride
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The monodesulfonylation reaction of N,N-bis(methylsulfonyl)-, N,N- bis(phenylsulfonyl)-, and N,N-bis(p-tolylsulfonyl)arylamines easily proceeded using tetrabutylammonium fluoride in tetrahydrofuran under mild conditions to give the corresponding N-monosulfonylarylamines in excellent yields.
- Yasuhara, Akito,Kameda, Mitsuyoshi,Sakamoto, Takao
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p. 809 - 812
(2007/10/03)
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- Inhibitors of acyl-CoA:cholesterol O-acetyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylmethyl-N'-arylureas
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A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity. From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively).
- Tanaka, Akira,Terasawa, Takeshi,Hagihara, Hiroyuki,Sakuma, Yuri,Ishibe, Noriko,Sawada, Masae,Takasugi, Hisashi,Tanaka, Hirokazu
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- Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry
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Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with "nonstabilized" phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl 3-pyridyl ketone determined the stereoselectivity.G
- Takeuchi, Kumiko,Paschal, Jonathan W.,Loncharich, Richard J.
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p. 156 - 168
(2007/10/02)
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