6311-23-5Relevant articles and documents
Synthesis, Antimicrobial, Anti-virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides
Al-Mahmoudy, Amany M. M.,Almalki, Ahmad J.,Hegazy, Wael A. H.,Ibrahim, Tarek S.,Mohamed, Mamdouh F. A.,Taher, Ehab S.,Youns, Mahmoud
, (2022/01/24)
Since the synthesis of prontosil the first prodrug shares their chemical moiety, sulfona-mides exhibit diverse modes of actions to serve as antimicrobials, diuretics, antidiabetics, and other clinical applications. This inspiring chemical nucleus has prom
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Late-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C?H Activation
Weis, Erik,Johansson, Magnus J.,Martín-Matute, Belén
supporting information, p. 18188 - 18200 (2021/11/22)
The functionalization of C?H bonds, ubiquitous in drugs and drug-like molecules, represents an important synthetic strategy with the potential to streamline the drug-discovery process. Late-stage aromatic C?N bond–forming reactions are highly desirable, but despite their significance, accessing aminated analogues through direct and selective amination of C?H bonds remains a challenging goal. The method presented herein enables the amination of a wide array of benzoic acids with high selectivity. The robustness of the system is manifested by the large number of functional groups tolerated, which allowed the amination of a diverse array of marketed drugs and drug-like molecules. Furthermore, the introduction of a synthetic handle enabled expeditious access to targeted drug-delivery conjugates, PROTACs, and probes for chemical biology. This rapid access to valuable analogues, combined with operational simplicity and applicability to high-throughput experimentation has the potential to aid and considerably accelerate drug discovery.
Nickel-mediated C(sp2)-H amidation in synthesis of secondary sulfonamides via sulfonyl azides as amino source
Xu, Peng,Ding, Peng-Fei,Zhang, Mei-Qi,Xia, Yu-Shi,Xie, Ting
, (2021/02/16)
In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp2)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp2)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which might proceed a Ni(III)/Ni(I) catalytic cycle. We also applied sulfonamide compound in OLEDs, which exhibits the certain application potential in OLEDs field.
Melatonin derivatives combat with inflammation-related cancer by targeting the Main Culprit STAT3
Ma, Shumeng,Zhu, Longqing,Fan, Xiaohong,Luo, Tian,Liu, Dan,Liang, Ziyi,Hu, Xiaoling,Shi, Tao,Tan, Wen,Wang, Zhen
, (2020/12/02)
The combination between two well-studied bioactive compounds melatonin and salicylic acid with proper modifications unexpectedly creates a sharp pair of “scissors” cutting off the vicious connection between inflammation and cancer by targeting a key contributor Signal Transducers and Activators of Transcription 3 (STAT3) in the two pathological processes. A representative compound P-3 with IC50 values on each tested cell line ranging from 7.37 to 18.62 μM among the designed melatonin derivatives is equipped with the ability of curbing inflammation-promoting cancer by down-regulating the expression, activation and nuclear translocation of STAT3, breaking the feedforward loop of STAT3 activation by decreasing the expression of pro-tumorigenic cytokines, and inducing cell apoptosis through ROS triggered Cyto-c/Caspase-3 pathway. This study suggests that the melatonin derivative P-3 is likely to become a promising chemical structure for developing the novel anti-cancer agents taking effect through hindering the mutual-promoting processes between inflammation and cancer.
Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant
Beccalli, Egle M.,Broggini, Gianluigi,Foschi, Francesca,Lo Presti, Leonardo,Loro, Camilla,Oble, Julie,Poli, Giovanni,Sala, Roberto
supporting information, (2020/02/28)
The palladium-catalyzed aminoazidation of aminoalkenes yielding azidomethyl-substituted nitrogen-containing heterocycles was developed. The procedure requires oxidative conditions and occurs at room temperature in the presence of hydrogen peroxide and NaN3 as the azide source. These conditions provide selective exo-cyclization/azidation of the carbon-carbon double bond, furnishing a versatile approach toward five-, six-, and seven-membered heterocyclic rings.
Hydroxamic acid with benzenesulfonamide: An effective scaffold for the development of broad-spectrum metallo-β-lactamase inhibitors
Li, Jia-Qi,Chen, Cheng,Yao, Min,Sun, Le-Yun,Gao, Han,Chigan, Jiazhu,Yang, Ke-Wu
, (2020/11/11)
Given that β-lactam antibiotic resistance mediated by metallo-β-lactamases (MβLs) seriously threatens human health, we designed and synthesized nineteen hydroxamic acids with benzenesulfonamide, which exhibited broad-spectrum inhibition against four teste
Palladium-catalyzed [5+1] annulation of salicylic acid derivatives and propargylic carbonates
Sato, Kazuya,Ogiwara, Yohei,Sakai, Norio
supporting information, p. 1595 - 1602 (2020/12/29)
A palladium-catalyzed annulation reaction between salicylic acid derivatives and propargylic carbonates via the cleavage of a propargylic carbonoxygen bond is described. This rare annulation reaction uses propargylic compounds as the C1 component for hete
Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information, p. 12724 - 12729 (2019/11/05)
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
INHIBITORS OF OPLOPHORUS LUCIFERASE-DERIVED BIOLUMINESCENT COMPLEXES
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Paragraph 00175; 00177-00178; 00233; 00250; 00252-00253, (2019/12/25)
Compounds that may selectively inhibit Oplophorus luciferase-derived bioluminescent complexes, e.g., NanoBiT? bioluminescent complex, are disclosed as well as compositions and kits comprising the compounds, and methods of using the compounds. The compounds are of formula (I) wherein R1-R4 and p and q are as defined in the claims.
