Convenient Synthesis of Some New Thiophene, Pyrazole, and Thiazole Derivatives Bearing Biologically Active Sulfonyl Guanidine Moiety

Fouad, Sawsan A.; El-Gendey, Marwa S.; Ahmed, E. M.; Hessein, Sadia A.; Ammar, Yousry A.; Zaki, Yasser H.

doi:10.1080/10406638.2021.1988999

Cited by 7 publications

(2 citation statements)

References 51 publications

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“…20 We describe here the synthesis of α-aminophosphonates derivatives, which were evaluated against carcinoma breast cancer and normal human PBMC cells, as a continuation of our prior work in the synthesis of biologically active heterocycles. [21][22][23][24][25][26][27] New alpha-aminophosphonate derivatives have been designed and manufactured. Hence, the chemical composition of the synthesized compounds were elucidated by spectroscopy, such as 13 C NMR, elemental analysis, infrared (IR) and 1 HNMR.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Spectroscopic Studies of Some New α-Aminophosphonate Analogues Derived from 4-Hydroxybenzaldehyde with Special Reference to Anticancer Activity

Ali¹,

Alotaibi²,

Zaki³

et al. 2022

DDDT

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Introduction As biological activity components, α-aminophosphonates and their moieties play important roles in medicinal chemistry. Alpha-phosphonic acids are significant α-amino acid counterparts. Due to its strong biological activity, this class of molecule has recently been discovered to have numerous medical applications. Results and Discussion A new class of α-aminophosphonates and arylidene derivatives was synthesized. Various spectroscopic and elemental analyses were used to confirm the prepared products. The produced materials were tested as anticancer against breast carcinoma cells and normal human cells (PBMC). Besides the analysis results, it was found that ( 7b, 4c, 5k, 6, 5a, 7c, 5f, 5b , and 5g ) against MCF-7 line cells. As a reference anticancer drug, 5-fluorouracil was used. The anticancer activities showed that the compounds 7b, 4c , containing α-aminophosphonate and Schiff base groups, respectively, showed high inhibition activity against the MCF-7 cell line, with 94.32% and 92.45% inhibition compared to the inhibition by 5-FU with 96.02% inhibition. The results showed that the compounds 5k, 7b, 6 , and 5a , respectively, had very low activity against normal human cells PBMC, with 12.77%, 13%, 13.13%, and 17.88% inhibition compared to the inhibition by 5-FU with 12.50% inhibition. The binding energy for non-bonding interactions between the ligand (studied compounds) and receptor, thymidylate synthase, was determined using molecular docking (pdb code: 1AN5). Conclusion α-aminophosphonate derivatives, arylidines, and disphosphonate derivatives derived from 4-hydroxybenzaldehyde were synthesized, purified, elucidated by spectroscopic analysis, and finally tested against carcinoma breast cancer to give high to moderate to low activity.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Spectroscopic Studies of Some New α-Aminophosphonate Analogues Derived from 4-Hydroxybenzaldehyde with Special Reference to Anticancer Activity

Ali¹,

Alotaibi²,

Zaki³

et al. 2022

DDDT

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“…The suppression of PR by drugs known as Selective Progesterone Receptor Modulators (SPRMs), which compete with the hormone progesterone, prevents cancer cells from proliferating [16]. In continuation of our recent work aimed at the synthesis of biologically active compounds [17][18][19][20][21], we intend to synthesize a series of 4-aryl-2-phosphonomethyl-4-oxobutanenitriles using the aromatic aldehyde and 2-dialkylphosphonomethylpropenenitriles in this work.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Efficient Approach to the Synthesis of 4-Aryl-2-dialkylphosphonomethyl-4-oxobutanenitrile

Yaccoubi

Elleuch

Mohamed

et al. 2022

Molbank

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In this work, we describe a simple and easy synthetic approach to variously 4-aryl-2-alkylphosphonomethyl-4-oxobutanenitrile based on the reaction of aromatic aldehydes with phosphorylated Michael’s acceptors in good yields. A general mechanism for the reactions was also proposed. Characterization of the products was carried out by several spectroscopic tools, including Infrared and Nuclear Magnetic Resonance Spectroscopies (1H, 13C, and 31P-NMR). Molecular docking studies were conducted on the synthesized materials against (1UK4) the crystal structure of the SARS Coronavirus Main Proteinase (3CLpro) to study the antiviral activity of these compounds and against (1E3K) the Human Progesterone Receptor to study the anticancer activity of these compounds. We found that compound (5i) was the best one in both antiviral and anticancer activity (according to the binding energy values).

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Synthesis and antimicrobial evaluation of some novel heterocyclic compounds based on azo chromene moiety

Elhaleem,

Fouad,

Hessein

et al. 2024

J IRAN CHEM SOC

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Convenient Synthesis of Some New Thiophene, Pyrazole, and Thiazole Derivatives Bearing Biologically Active Sulfonyl Guanidine Moiety

Cited by 7 publications

References 51 publications

Design, Synthesis, and Spectroscopic Studies of Some New α-Aminophosphonate Analogues Derived from 4-Hydroxybenzaldehyde with Special Reference to Anticancer Activity

Design, Synthesis, and Spectroscopic Studies of Some New α-Aminophosphonate Analogues Derived from 4-Hydroxybenzaldehyde with Special Reference to Anticancer Activity

A Simple and Efficient Approach to the Synthesis of 4-Aryl-2-dialkylphosphonomethyl-4-oxobutanenitrile

Synthesis and antimicrobial evaluation of some novel heterocyclic compounds based on azo chromene moiety

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