Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals

Alazemi, Abdulrahman M.; Dawood, Kamal M.; Al-Matar, Hamad M.; Tohamy, Wael M.

doi:10.1039/d3ra04558g

Cited by 3 publications

(1 citation statement)

References 81 publications

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“…The best-known drugs derived from it are acetylsalicylic acid or Aspirin ® -with anti-inflammatory, antipyretic, and anticoagulant effects [17]-and mesalazine, which is used to treat inflammatory bowel diseases [18]. Salicylanilides, commercially available, e.g., as niclosamide [19], rafoxanide [20], or closantel [21], are anthelmintics, but in recent years, their other biological effects have been discovered, e.g., anticancer [22] or antiviral [23], stimulating scientific interest in these simple and small molecules [24][25][26][27][28][29][30][31][32]. In addition to anticancer activity [33], for example, their herbicidal activity [34] or ability to inhibit acetylcholinesterase [35][36][37] can be mentioned.…”

Section: Introductionmentioning

confidence: 99%

Conformational and Chiroptical Properties of Salicylamide-Based Peptidomimetics

Raich,

Pauk,

Imramovsky

et al. 2024

Symmetry

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Optical rotation (OR), the most frequently used chiroptical method, is used for the characterization of newly synthesized or isolated compounds. Computational predictions of OR are, however, mainly used for the determination of the absolute configurations of chiral compounds, but they may also be used for the verification of conformational analysis results if the experimental values are known. Our computational study deals with the conformational analysis of flexible salicylamide-based peptidomimetics, starting with a conformation search, then a low-level ab initio preoptimization of the hundreds of conformations found, and, finally, a higher-level DFT optimization. For the resulting minima structures, Boltzmann populations were calculated, followed by OR calculations for all the populated conformers using the DFT method with various basis sets with diffuse functions. Weighted averages of the ORs were compared with experimental values, and the agreement, which ranged from excellent to moderate for various compounds, served as a verification of the conformational analysis results.

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Section: Introductionmentioning

confidence: 99%

Conformational and Chiroptical Properties of Salicylamide-Based Peptidomimetics

Raich,

Pauk,

Imramovsky

et al. 2024

Symmetry

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Synthesis and Anti-Breast Cancer Potency of Mono- and Bis-(pyrazolyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine) Derivatives as EGFR/CDK-2 Target Inhibitors

Salem,

Mahrous,

Ragab

et al. 2023

ACS Omega

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The target mono- and bis-(6-pyrazolyltriazolo-thiadiazine) derivatives 4a-c and 6a-d were synthesized using a straightforward protocol via reaction of 3-bromoacetylpyrazole 2 with 4-amino- s -triazole-3-thiols 3a-c and bis(4-amino-5-mercapto- s -triazol-3-yl)alkanes 5a-d , respectively. The bis(6-pyrazolyl- s -triazolo[3,4- b ][1,3,4]thiadiazine) derivatives 8a , b and 10 were also constructed by reaction of the triazolo[3,4- b ][1,3,4]thiadiazine-3-thiol 4c with the proper dibromo compounds 7a , b and 9 , respectively. Structures of the new substances were determined by spectroscopic and analytical data. Compounds 4b , 4c , and 6a showed potent cytotoxicity against MCF-7 (IC 50 = 3.16, 2.74, and 0.39 μM, respectively) and were safe against the MCF-10A cells. Compounds 4b , 4c , and 6a also showed promising dual EGFR and CDK-2 inhibition activities, particularly 6a was the most effective (IC 50 = 19.6 and 87.9 nM, respectively), better than Erlotinib and Roscovitine. Compound 6a treatment induced EGFR and CDK-2 enzyme inhibition by 97.18% and 94.11%, respectively, at 10 μM (the highest concentration). Compound 6a notably induced cell apoptosis in MCF-7 cells, increasing the cell population by total apoptosis 43.3% compared to 1.29% for the untreated control group, increasing the cell population at the S-phase by 39.2% compared to 18.6% (control).

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Clean and Efficient Green Protocol of N,N′-Bis(2-(arylazo)-2-(aroyl)vinyl)ethane-1,2-diamines in Aqueous Medium without Catalyst: Synthesis and Photophysical Characterization

Alazemi,

Dawood,

Al-Matar

et al. 2024

ACS Omega

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An interesting platform for the construction of novel N,N′-bis(2-(arylazo)-2-(aroyl)vinyl)ethane-1,2-diamines is reported in this work. These bis-arylazo compounds were assembled based on the reaction of ethylenediamine with various 2arylhydrazono-3-oxopropanals in aqueous conditions under both conventional stirring and microwave conditions at ambient temperature. The factors affecting the optimization conditions were intensively practiced. The structures of the new products were established from their spectroscopic analyses and X-ray single crystals. The photophysical behavior of the bis-arylazo derivatives was examined. The UV−vis spectra showed maximum absorption band in the range of 348−383 nm with molar extinction coefficients ranging from 0.89 × 10 4 to 4.02 × 10 4 M −1 cm −1 . The highest molar absorptivity coefficient (∼45 × 10 3 M −1 cm −1 ) was observed in CHCl 3 solvent. The fluorescence properties showed that some compounds were interesting fluorophore materials with high Stokes shifts. The photoluminescence study of some compounds was promising, with maximal emission peaks ranging between 417−436 nm.

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Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals

Abstract: The reaction of 3-oxo-2-arylhydrazonopropanals with acetoacetanilide in an equimolar ratio, under DBU/1,4-dioxane/microwave irradiation reaction conditions, resulted in chemoselective formation of 4-arylazo-5-hydroxy-benzamide derivatives.

Cited by 3 publications

References 81 publications

Conformational and Chiroptical Properties of Salicylamide-Based Peptidomimetics

Conformational and Chiroptical Properties of Salicylamide-Based Peptidomimetics

Synthesis and Anti-Breast Cancer Potency of Mono- and Bis-(pyrazolyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine) Derivatives as EGFR/CDK-2 Target Inhibitors

Clean and Efficient Green Protocol of N,N′-Bis(2-(arylazo)-2-(aroyl)vinyl)ethane-1,2-diamines in Aqueous Medium without Catalyst: Synthesis and Photophysical Characterization

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