Chemistry and pharmacological diversity of benzothiazepine—Excellent pathway to drug discovery

Ogunnupebi, Temitope A.; Ajani, Olayinka O.; Oduselu, Gbolahan O.; Elebiju, Oluwadunni F.; Adebiyi, Ezekiel

doi:10.1016/j.molstruc.2023.135071

Cited by 8 publications

(3 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nitrogen-based heterocyclic compounds have drawn interest of researchers over the years, due to their biological importance [1][2][3][4][5]. The dihydropyrimidine nucleus, a doubly unsaturated six-membered ring possessing two nitrogen atoms at positions 1 and 3, is one of the most important nitrogencontaining heterocycles which was first synthesized by Pietro Biginelli in 1891 in the multicomponent Biginelli reaction [6].…”

Section: Introductionmentioning

confidence: 99%

Recent progress in biological activities of dihydropyrimidine derivatives: An updated mini-review

Elshamsy,

Ali,

Osman

et al. 2023

Journal of advanced Biomedical and Pharmaceutical Sciences

View full text Add to dashboard Cite

Dihydropyrimidines (DHPMs) are a class of nitrogen-containing heterocycles that have attracted considerable interest due to their great significance in organic and medicinal chemistry. In recent years, many biologically active molecules featuring DHPM moiety have been synthesized and biologically evaluated, some of which have served as potential leads for critical unmet pathological conditions such as the antimitotic Monastrol and the antiviral GLS4, which entered clinical trials a few years ago. This review discusses briefly the recent advances in DHPM-based bioactive compounds, their biological activities, and their mechanisms of action, which could provide references for future developments of more potent and selective leads.

show abstract

Section: Introductionmentioning

confidence: 99%

Recent progress in biological activities of dihydropyrimidine derivatives: An updated mini-review

Elshamsy,

Ali,

Osman

et al. 2023

Journal of advanced Biomedical and Pharmaceutical Sciences

View full text Add to dashboard Cite

show abstract

“…To develop the one-pot reaction for the synthesis of benzo-[f ] [1,2]thiazepine 1,1-dioxide from benzo[d]isothiazole 1,1-dioxides with alkenes, the compatibility of the solvent was investigated first. When the ring-expansion reaction was carried out in ethyl acetate, the result was unsatisfactory.…”

mentioning

confidence: 99%

“…Benzothiazepine derivatives show various biological activities and many of them can be used as potential anticancer, antidiabetic, anti-inflammatory, antiviral and antimalarial agents, CNS depressants, antiplatelet aggregators, anti-cholinesterase inhibitors, anticonvulsant agents, Ca 2+ channel antagonists, and vasodilators. 1 Recently, it was discovered that the 1,2-benzothiazepine 1,1-dioxide derivatives listed in Fig. 1 also show excellent biological activities.…”

mentioning

confidence: 99%

Synthesis of benzo[f][1,2]thiazepine 1,1-dioxides based on the visible-light-mediated aza Paternò–Büchi reaction of benzo[d]isothiazole 1,1-dioxides with alkenes

Wang,

Liu,

Zhang

et al. 2023

Chem. Commun.

View full text Add to dashboard Cite

show abstract

Synthesis and Cancer Cell Cytotoxicity of 6‐, 7‐, or 8‐Substituted 2‐(Hetero)aryl‐4‐(4‐(Hetero)aryl‐2‐Oxobut‐3‐en‐1‐Ylidene)Benzothiazepanes

Magdalenic,

Morillon,

De Jonghe

et al. 2024

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Cancer chemotherapy is continuously challenged by serious complications like pronounced side effects and multidrug resistance (MDR). Natural products, such as curcumin, offer promising alternatives due to their diverse biological applications and low toxicity. However, curcumin's clinical utility is limited by poor bioavailability, rapid metabolism, and non‐specific (PAINS) activity. Building on previous findings, this study explored the structural modification of curcumin‐inspired benzothiazepane derivatives in an attempt to enhance their therapeutic potential through modifications of the two peripheral (hetero)aromatic rings and the benzothiazepane scaffold. In this way, eight new 2‐(hetero)aryl‐4‐(4‐(hetero)aryl‐2‐oxobut‐3‐en‐1‐ylidene)benzothiazepanes and two 4‐thiobutan‐2‐one “double Michael addition” derivatives were synthesized and tested for cytotoxicity against a panel of eight cancer cell lines. The screening results indicated that bis‐(4‐hydroxyphenyl) analogs bearing a chlorinated benzothiazepane ring exhibited the highest potency and broad‐spectrum activity at the low micromolar range. Bis‐substitutions with 3‐pyridinyl and 2‐furyl groups showed less potent but more specific activity profiles, potentially reducing PAINS effects. 2‐Aminothiophenol‐derived double Michael addition products demonstrated increased broad‐spectrum activity, highlighting the importance of the free aniline amino group for targeted effects. This study underscores the potential of benzothiazepane derivatives as viable cancer cell cytotoxic agents and provides useful insights for future optimization and evaluation.

show abstract

Chemistry and pharmacological diversity of benzothiazepine—Excellent pathway to drug discovery

Cited by 8 publications

References 48 publications

Recent progress in biological activities of dihydropyrimidine derivatives: An updated mini-review

Recent progress in biological activities of dihydropyrimidine derivatives: An updated mini-review

Synthesis of benzo[f][1,2]thiazepine 1,1-dioxides based on the visible-light-mediated aza Paternò–Büchi reaction of benzo[d]isothiazole 1,1-dioxides with alkenes

Synthesis and Cancer Cell Cytotoxicity of 6‐, 7‐, or 8‐Substituted 2‐(Hetero)aryl‐4‐(4‐(Hetero)aryl‐2‐Oxobut‐3‐en‐1‐Ylidene)Benzothiazepanes

Contact Info

Product

Resources

About