Retrosynthetic Approach to the Synthesis of Phenothiazines

Silberg, Ioan A.; Cormos, Gabriela; Oniciu, Daniela C.

doi:10.1016/s0065-2725(05)90003-2

Cited by 17 publications

(2 citation statements)

References 101 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Most syntheses of phenothiazine and azaphenothiazine ring systems proceeded through the Smiles rearrangement of appropriate aryl or azinyl sulfides [ 3 , 50 , 51 , 52 , 53 ]. Reaction of 4,4′-dichloro-3,3′-diquinolinyl sulfide 1 with amines is considered to run via nucleophilic monosubstitution of one chlorine atom to form sulfide A ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

14-Substituted Diquinothiazines as a New Group of Anticancer Agents

et al. 2023

View full text Add to dashboard Cite

A series of novel double-angularly condensed diquinothiazines with aminoalkyl, amidoalkyl, sulfonamidoalkyl, and substituted phenyl groups was designed, synthesized, and evaluated for their anticancer activity against four selected human tumor cell lines (HTC116, SH-SY5Y, A549, and H1299). The cytotoxicity of the novel diquinothiazines was investigated against BEAS-2B cells. The activities of the compounds were compared to etoposide. Among them, compounds with aminoalkyl and phenyl groups showed excellent broad-spectrum anticancer activity. The most active 14-(methylthiophenyl)diquinothiazine, 3c, showed low cytotoxicity against BEAS-2B cells and high activity against tumor cell lines HTC116, SH-SY5Y, A549, and H1299, with IC50 values of 2.3 µM, 2.7 µM, 17.2 µM, and 2.7 µM, respectively (etopiside 8.6 µM, 3.9 µM, 44.8 µM, and 0.6, respectively). Live long-term microscopic observations of cell survival using the starting molecule M0 were also performed. Flow cytometry showed the proapoptotic effects of the studied diquinothiazines. Inhibition of the cell cycle in the S phase was observed, which is associated with damage to nucleic acids and connected to DNA replication arrest.

show abstract

Section: Resultsmentioning

confidence: 99%

14-Substituted Diquinothiazines as a New Group of Anticancer Agents

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Phenothiazines were reviewed in the 50s and 70s [7–10] and exhaustively in a monograph edited by Gupta in the 80s [11]. Recently, a retrosynthetic approach to the synthesis of phenothiazines was described [12]. Syntheses and properties of monoazaphenothiazines were reviewed in 1990 in Polish based on 78 references [13].…”

Section: Introductionmentioning

confidence: 99%