134812-30-9Relevant academic research and scientific papers
Structure activity relationship and optimization of N-(3-(2-aminothiazol-4-yl)aryl)benzenesulfonamides as anti-cancer compounds against sensitive and resistant cells
Ronco, Cyril,Millet, Antoine,Plaisant, Magali,Abbe, Patricia,Hamouda-Tekaya, Nedra,Rocchi, Stéphane,Benhida, Rachid
, p. 2192 - 2196 (2017)
We recently described a new family of bioactive molecules with interesting anti-cancer activities: the N-(4-(3-aminophenyl)thiazol-2-yl)acetamides. The lead compound of the series (1) displays significant anti-proliferative and cytotoxic activities against a panel of cancer cell lines, either sensitive or resistant to standard treatments. This molecule also shows a good pharmacological profile and high in vivo potency towards mice xenografts, without signs of toxicity on the animals. In the present article, we disclose the structure-activity relationships of this lead compound, which have provided clear information about the replacement of the acetamide function and the substitution pattern of the benzenesulfonamide ring. An improved high-yielding synthetic procedure towards these compounds has also been developed. Our drug design resulted in potency enhancement of 1, our new optimized lead compound being 19. These findings are of great interest to further improve this scaffold for the development of future clinical candidates.
Preparation method for terpyridine pyridinium complex and application thereof in reverse transcriptase inhibition
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, (2019/01/16)
The invention belongs to the field of research and development of HIV inhibitors, and discloses a preparation method for a terpyridine pyridinium (II) complex and application thereof in HIV reverse transcriptase inhibition. The structure of a cationic moiety of the terpyridine pyridinium (II) complex is as shown in a formula I. A preparation process for the terpyridine pyridinium (II) complex is optimized, the raw material cost is low, and the reaction time is short. The obtained complex is high in purity and yield and has good water solubility and excellent spectral properties. The terpyridine pyridinium (II) complex has the capability of selective binding to a TAR region on HIV RNA, and can block the reverse transcription process of viral RNA by reverse transcriptase and inhibit the replication of viral RNA. The terpyridine pyridinium (II) complex is a highly affinitive HIV RNA selective binding reagent and a highly active HIV reverse transcriptase inhibitor, and is an HIV drug having a great application potential.
SUBSTITUTED HYDROPHOBIC BENZENE SULFONAMIDE THIAZOLE COMPOUNDS FOR USE IN TREATING CANCER
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, (2017/02/24)
The present invention relates to compound of general formula (I) R1 is selected from H, aryl and alkyl, R2 is selected from H, alkyl, aryl and CO-R6; R3 is selected from H, halogen, alkyl, alkenyl, alkynyl, aryl, NHR7, NR7R8, OR7 and SR7; R4 is selected from(C6-C12) alkyl, (C2-C12) alkenyl, (C2-C12) alkynyl and (C6-C10) aryl, R5 represents H, R6, aryl, OH, OR6, O-aryl, SH, SR6, S-aryl, CN, NO2, CF3, COOR6, SO2NR6R7, CONR6R7, NH2, NHR6, NH-aryl, NR6R7, NHCOR6 or aminoacyl; R6 is alkyl optionally substituted with halogen, OH, SH, NH2, O-alkyl, S-alkyl, NH- alkyl or NH-di(alkyl); R7 and R8 identical or different are H or alkyl optionally substituted with halogen, OH, SH, NH2, O-alkyl, S-alkyl, NH-alkyl or NH-di (alkyl), their pharmaceutically acceptable salts and/or isomers, tautomers, solvates or isotopic variations thereof. The compounds are useful for the treatment of cancers.
Discovery and Optimization of N-(4-(3-Aminophenyl)thiazol-2-yl)acetamide as a Novel Scaffold Active against Sensitive and Resistant Cancer Cells
Millet, Antoine,Plaisant, Magali,Ronco, Cyril,Cerezo, Micha?l,Abbe, Patricia,Jaune, Emilie,Cavazza, Elisa,Rocchi, Stéphane,Benhida, Rachid
, p. 8276 - 8292 (2016/10/03)
Cancer is the second cause of deaths worldwide and is forecasted to affect more that 22 million people in 2020. Despite dramatic improvement in its care over the last two decades, the treatment of resistant forms of cancer is still an unmet challenge. Thus, innovative and efficient treatments are still needed. In this context, we report herein the synthesis and the evaluation of a new class of bioactive molecules belonging to the N-(4-(3-aminophenyl(thiazol-2-yl)acetamide family. Structure-activity relationships could be driven and resulted in the discovery of lead compound 6b. The latter display high in vitro potency against both sensitive and resistant cancer cell lines on three models: melanoma, pancreatic cancer, and chronic myeloid leukemia (CML). 6b leads to cell death by concomitant induction of apoptosis and autophagy, shows good pharmacokinetic properties, and demonstrates a significant reduction of tumor growth in vivo on A375 xenograft model in mice.
NEW BENZENE SULFONAMIDE THIAZOLE COMPOUNDS
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, (2014/05/24)
The present invention relates to compound of general formula (1) wherein R1 represents C6-C10 aryl comprising one or two fused rings, wherein from 2 to 5 carbon atoms may be replaced with a heteroatom selected from O, S and NR6, and eventually substituted with from 5 to 11 substituants selected from R6, halo, CN, NO2, CF3, OCF3, COOR6, OCOR6, SO2NR6R7, CONR6R7, NR6R7, NR6COR7, (CH2)P- NR6R7, (CH2)P- OR6 and (CH2)PSR6, as well as, if appropriate, their pharmaceutically acceptable salts and/or isomers, tautomers, solvates or isotopic variations thereof. The compounds are useful for the treatment of cancers.
Design of novel RNA ligands that bind stem-bulge HIV-1 TAR RNA
Duca, Maria,Malnuit, Vincent,Barbault, Florent,Benhida, Rachid
supporting information; experimental part, p. 6162 - 6164 (2010/11/04)
We report here the rational design and the synthesis of a new series of RNA ligands. These molecules are constituted of various binding motifs that interact cooperatively with HIV-1 TAR RNA, used as a model.
Incorporation of a novel nucleobase allows stable oligonucleotide-directed triple helix formation at the target sequence containing a purine pyrimidine interruption
Guianvarc'h,Benhida,Fourrey,Maurisse,Sun
, p. 1814 - 1815 (2007/10/03)
Thermal denaturation experiments have established that an oligonucleotide incorporating the artificial nucleobase S, does form a stable triplex with a double stranded DNA which exhibits a pyrimidine interruption within the oligopurine sequence.
