Synthesis of N-Azaaryl Anilines: An Efficient Protocol via Smiles Rearrangement

Xia, Shuai; Wang, Liying; Sun, Hengzhi; Yue, Huan; Wang, Xiuhua; Tan, Jia‐Lian; Wang, Yin; Hou, Di; He, Xiaoyan; Mun, K. R.; Kumar, Brijesh; Zuo, Hua; Shin, Dong‐Soo

doi:10.5012/bkcs.2013.34.2.394

Cited by 11 publications

(3 citation statements)

References 29 publications

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“…A LECO 630–200–200 TRUSPEC CHNS microanalyzer was used for elemental analysis and the data obtained was within ±0.4% of the calculated results. Compounds 2 – 4 were prepared according to the literature [ 55 , 57 ].…”

Section: Experimental Set-upmentioning

confidence: 99%

N -Arylacetamide derivatives of methyl 1,2-benzothiazine-3-carboxylate as potential drug candidates for urease inhibition

et al. 2023

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Urease enzyme is an infectious factor that provokes the growth and colonization of virulence pathogenic bacteria in humans. To overcome the deleterious effects of bacterial infections, inhibition of urease enzyme is one of the promising approaches. The current study is designed to synthesize new 1,2-benzothiazine- N -arylacetamide derivatives 5 ( a-n ) that can effectively provide a new drug candidate to avoid bacterial infections by urease inhibition. After structural elucidation by FT-IR, proton and carbon-13 NMR and mass spectroscopy, the synthesized compounds 5 ( a-n ) were investigated to evaluate their inhibitory potential against urease enzyme. In vitro analysis against positive control of thiourea indicated that all the synthesized compounds have strong inhibitory strengths as compared to the reference drug. Compound 5k , being the most potent inhibitor, strongly inhibited the urease enzymes and revealed an IC 50 value of 9.8 ± 0.023 µM when compared with the IC 50 of thiourea (22.3 ± 0.031 µM)—a far more robust inhibitory potential. Docking studies of 5k within the urease active site revealed various significant interactions such as H-bond, π-alkyl with amino acid residues like Val744, Lys716, Ala16, Glu7452, Ala37 and Asp730.

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Section: Experimental Set-upmentioning

confidence: 99%

N -Arylacetamide derivatives of methyl 1,2-benzothiazine-3-carboxylate as potential drug candidates for urease inhibition

et al. 2023

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“…The IR spectra of compounds 5a,b and 9a,b showed a characteristic forked peak at 3425 and 3336 cm −1 for compounds 5a-b, 3417 and 3332 cm −1 for compound 9a, and 3402 and 3321 cm −1 for compound 9b, attributed to their amino groups. Compounds 7a-c and 11a-c were synthesized through the reaction of compounds 6a and 10a, respectively, with substituted phenols in the presence of potassium carbonate [67]. Similarly, heating of the substituted phenols and K 2 CO 3 with compounds 6b and 10b afforded compounds 7d-f and 11d-f, respectively.…”

Section: Screening Of Compounds Using Hcv Gt 1b Replicon Assaymentioning

confidence: 99%

Novel 6-Aminoquinazolinone Derivatives as Potential Cross GT1-4 HCV NS5B Inhibitors

Nasr

Aboshanab

Mpekoulis

et al. 2022

Viruses

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Chronic hepatitis C virus (HCV) infections are a worldwide medical problem responsible for diverse types of liver diseases. The NS5B polymerase enzyme has become a very interesting target for the development of anti-HCV drugs owing to its fundamental role in viral replication. Here we report the synthesis of a novel series of 1-substituted phenyl-4(1H)-quinazolinone and 2-methyl-1-substituted phenyl-4(1H)-quinazolinone derivatives and evaluate their activity against HCV in HCV subgenomic replicon assays. The biological data revealed that compound 11a showed the highest activity against HCV GT1b at a micromolar concentration (EC50 = 0.984 µM) followed by compound 11b (EC50 = 1.38 µM). Both compounds 11a and 11b had high selectivity indices (SI = CC50/EC50), 160.71 and 71.75, respectively, which make them very interesting candidates for further development of more potent and selective anti-HCV agents.

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“…À uma solução de 11b (0,5 mL, 5,5 mmol) e carbonato de potássio (1,13 g, 8,2 mmol) em diclorometano (10 mL) foi gotejada uma solução de cloreto de cloroacetila (0,652 mL, 8,2 mmol) em diclorometano (5 mL) lentamente, procedimento realizado em banho de gelo. Após adição de todo o cloreto de cloroacetila em diclorometano, a reação permaneceu à temperatura ambiente e sob agitação por 5 horas (XIA et al, 2013). Uma solução de brometo de tetranbutilamônio (0,0027g, 0,0085 mmol) foi preparada em éter etílico (0,8 mL) e hidróxido de sódio 50% aquoso (0,4 mL), a ela foi adicionado o composto 10 (0,10 g, 0,17 mmol) que permaneceu em solução por 16 horas para formação do alcóxido.…”

Section: Monotritilação Do áLcool Batílicounclassified

Síntese de novos fosfolipídios antitumorais para a inibição da enzima trifosfato de citidina (CTP)

Antônio de Oliveira Neto

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Synthesis of N-Azaaryl Anilines: An Efficient Protocol via Smiles Rearrangement

Cited by 11 publications

References 29 publications

N -Arylacetamide derivatives of methyl 1,2-benzothiazine-3-carboxylate as potential drug candidates for urease inhibition

N -Arylacetamide derivatives of methyl 1,2-benzothiazine-3-carboxylate as potential drug candidates for urease inhibition

Novel 6-Aminoquinazolinone Derivatives as Potential Cross GT1-4 HCV NS5B Inhibitors

Síntese de novos fosfolipídios antitumorais para a inibição da enzima trifosfato de citidina (CTP)

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