Synthesis, Antimicrobial and Antioxidant Activities of Pyrimidinyl Benzothiazine Carboxamides

Rekha, T. N.; Panga, Siva Sankar; Zyryanov, Grigory V.; Sravya, G.; Reddy, N. Bakthavatchala; Vasikarla, Kamala Prasad; Padmaja, A.; Padmavathi, V.

doi:10.1002/slct.201900525

Cited by 6 publications

(2 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…When seeking mechanistic information on the reaction starting from compound 1a , we realized that depending on the basicity of the system (i.e., on the amount of t -BuOK applied), the reaction could result either in the previously described benzisothiazole 2a ( 26 ) or in an unexpected benzothiazine derivative 3a ( Scheme 2 ), the latter being again a molecular framework in the focus of recent pharmacological interest. 27 − 35 Hereby we explore the mechanism of this highly complex reaction and demonstrate that it is possible to selectively influence the outcome of the reaction toward any of the two different products. The corresponding experimental and computational studies are described below, with further details disclosed in the Supporting Information (SI).…”

Section: Resultsmentioning

confidence: 99%

Basicity-Tuned Reactivity: diaza-[1,2]-Wittig versus diaza-[1,3]-Wittig Rearrangements of 3,4-Dihydro-2H-1,2,3-benzothiadiazine 1,1-Dioxides

et al. 2020

View full text Add to dashboard Cite

The base-induced ( t -BuOK) rearrangement reactions of 3,4-dihydro-2 H -1,2,3-benzothiadiazine 1,1-dioxides result in a ring opening along the N–N bond, followed by ring closure with the formation of new C–N bonds. The position of the newly formed C–N bond can selectively be tuned by the amount of the base, providing access to new, pharmacologically interesting ring systems with high yield. While with 2 equiv of t -BuOK 1,2-benzisothiazoles can be obtained in a diaza -[1,2]-Wittig reaction, with 6 equiv of the base 1,2-benzothiazine 1,1-dioxides can be prepared in most cases as the main product, in a diaza -[1,3]-Wittig reaction. DFT calculations and detailed NMR studies clarified the mechanism, with a mono- or dianionic key intermediate, depending on the amount of the reactant base. Also, the role of an enamide intermediate formed during the workup of the highly basic (6 equiv of base) reaction was clarified. The substrate scope of the reaction was also explored in detail.

show abstract

Section: Resultsmentioning

confidence: 99%

Basicity-Tuned Reactivity: diaza-[1,2]-Wittig versus diaza-[1,3]-Wittig Rearrangements of 3,4-Dihydro-2H-1,2,3-benzothiadiazine 1,1-Dioxides

et al. 2020

View full text Add to dashboard Cite

show abstract

“…2-Aminopyrimidines with pyrrole substituents represent molecular systems, which could be particularly promising for medicinal chemistry, due to the presence of two pharmacologically active units in their structure. This assumption is supported by the fact that among pyrrole–aminopyrimidines there are inhibitors of JAK2 (Janus kinase 2) [ 20 , 21 ], Cdc7 kinase (Cell division cycle 7-related protein kinase) [ 22 , 23 ], and Polo-like kinase 1 [ 24 ], as well as representatives with prominent antifungal activity against Aspergillus niger [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

et al. 2021

View full text Add to dashboard Cite

An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

show abstract

Antioxidant and Antitumor Potential of Some Benzoxazines Against MCF‐7 Cell Lines Using InVitro and InSilico Approaches

Mouada,

Hachama,

Zafar

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Cancer remains a severe global health problem, with its incidence constantly increasing.. Among many varieties of cancer, breast cancer persists as a prevalent global health concern, with its occurrence continually ascending. Among women, breast cancer is a significant cause of illness and death globally. This study examined the antioxidant and anticancer effects of two resynthesized benzoxazine derivatives, OBOP‐01 and OBOP‐02, on human breast cancer cells. The chemicals investigated had intense antioxidant action against DPPH, H2O2, and ABTS free radicals. Furthermore, we evaluated cell viability by converting yellow MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl tetrazolium bromide) into purple formazan, dependent on mitochondrial function. Both compounds had IC50 values of 1.52±0.02 mM and 1.72±0.02 mM respectively. Moreover, toxicity predictions using the ProTox‐III webserver showed that the benzoxazines studied have lower LD50 values compared to doxorubicin, suggesting greater safety. We also used Density Functional Theory (DFT) to analyze OBOP‐01 and OBOP‐02′s electrical interactions and properties. Gaining insight into these interactions is essential for understanding the compounds′ potential applications and properties. According to theoretical studies using molecular docking, the derivatives may interact with estrogen receptor alpha (ERα) (ID: 7NDO), a key target molecule in the development of breast cancer. Additionally, the complex OBOP‐01 – ERα′s molecular dynamics simulations were conducted for 100 nanoseconds. These simulations revealed essential details regarding the complex's dynamic behavior in a physiological system.

show abstract

Synthesis, Antimicrobial and Antioxidant Activities of Pyrimidinyl Benzothiazine Carboxamides

Cited by 6 publications

References 25 publications

Basicity-Tuned Reactivity: diaza-[1,2]-Wittig versus diaza-[1,3]-Wittig Rearrangements of 3,4-Dihydro-2H-1,2,3-benzothiadiazine 1,1-Dioxides

Basicity-Tuned Reactivity: diaza-[1,2]-Wittig versus diaza-[1,3]-Wittig Rearrangements of 3,4-Dihydro-2H-1,2,3-benzothiadiazine 1,1-Dioxides

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

Antioxidant and Antitumor Potential of Some Benzoxazines Against MCF‐7 Cell Lines Using InVitro and InSilico Approaches

Contact Info

Product

Resources

About