New series of 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine thione (THTT) derivatives: Synthesis and potent antileishmanial activity

Arshad, Najma; Hashim, Jamshed; Ullah, Irfan; Minhas, Muhammad Ali; Aslam, Javeria; Ashraf, Tahira; Hamid, Syeda Zehra; Iqbal, Tahseen; Javed, Shumaila

doi:10.1016/j.bmcl.2018.07.045

Cited by 22 publications

(13 citation statements)

References 27 publications

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“…After 30 minutes of stirring, resulted precipitates were filtered and recrystallized from EtOH to give THTT (7a-f) as a pure white solid. Spectroscopic analysis of the THTT 7a-f (series A) was found in good agreement with previously reported data (Arshad et al, 2018).…”

Section: General Experimental Detailssupporting

confidence: 91%

“…General procedure for the synthesis of Series-B (3,5disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thiones, 8a-d) For the preparation of THTT products (8a-d), the same procedure was used as for series A, except that initially glycine (10 mmol) was used instead of alkyl-, or aralkylamine. Spectroscopic analysis of the THTT 8a-d (series B) was found in good agreement with previously reported data (Arshad et al, 2018).…”

Section: General Experimental Detailssupporting

confidence: 91%

“…The resulting THTT (9a-f) as pure white solid were subjected for characterization. Spectroscopic analysis of the THTT 9a-f (series C) was found in good agreement with previously reported data (Arshad et al, 2018). Scheme 1: Synthetic routes to tetrahydro thiadiazine thiones series A (7a˗f), series B (8a˗d), series C (9a˗f) and series D (10a˗d).…”

Section: General Experimental Detailssupporting

confidence: 89%

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2021

Pak. J. Pharm. Sci

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Four series of tetrahydro-2H-1,3,5-thiadiazine thione derivatives were screened for their in vitro antiproliferative activities against two human cancerous PC3 and HeLa cell lines. The cytotoxicity of all the compounds (series A-D) was also determined on mammalian mouse fibroblast 3T3 cells. Most of the compounds showed significant anticancer potential against both cancer cell lines within the range of IC 50 = 6.4-29.9 and 2.4-23.8 M respectively when compared with standard doxorubicin (IC 50 = 0.3 M). All compounds demonstrated a notable selectivity for Hela cells and found either non-toxic or relatively less toxic for 3T3 cell lines model. The structure-activity relationship indicated that antiproliferative activity mainly influenced by the nature and position of substituents at thidiazine nucleus. In general, the presence of aryl groups for example 3,4-(OMe) 2 .Bzl and CH(Ph)Me at N-3 position resulted in a significant activity. Under enzymatic hydrolysis, complete conversion (100%) of ester derivative of thiadiazine thione (10a) into its acidic counterpart (7c) was achieved during 20 min which indicated that these types of THTT ester derivatives can be a possible lead for future investigations as prodrug anticancer probes.

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Section: General Experimental Detailssupporting

confidence: 91%

Section: General Experimental Detailssupporting

confidence: 91%

Section: General Experimental Detailssupporting

confidence: 89%

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2021

Pak. J. Pharm. Sci

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“…1,3,5-Thiadiazine-2-thione derivatives were attractive bioactive molecules and exhibited antibacterial (Mao et al, 2017), antifungal (Vicentini et al, 2002), herbicidal (Vicentini et al, 2005), anticancer (El-Shorbagi et al, 2018), antileishmanial (Arshad et al, 2018), antiepileptic (Semreen et al, 2010), antimalarial (Coro et al, 2006), antioxidant (Ji et al, 2004), antitubercular (Katiyar et al, 2003) and trypanocidal (Coro et al, 2005) activities. Notably, the agricultural application of 1,3,5-thiadiazine-2-thione derivatives has also attracted great attention by chemists and biologists in the last three decades.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

Yan

et al. 2019

PeerJ

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A series of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group was designed and synthesized. The structures of all the compounds were well characterized using 1H NMR, 13C NMR and high-resolution mass spectrometer, and further confirmed by the X-ray diffraction analysis of 8d. The antimicrobial activities of all the target compounds against Xanthomonas oryzae pv. oryzicola, X. oryzae pv. oryzae, Rhizoctonia solani and Fusarium graminearum were evaluated. The in vitro antimicrobial bioassays indicated that some title compounds exhibited noteworthy antimicrobial effects against the above strains. Notably, the compound N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)-2-(5-methyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acetamide (8a) displayed obvious antibacterial effects against X. oryzae pv. oryzicola and X. oryzae pv. oryzae at 100 μg/mL with the inhibition rates of 30% and 56%, respectively, which was better than the commercial bactericide thiodiazole-copper. In addition, the anti-R. solani EC50 value of 8a was 33.70 μg/mL, which was more effective than that of the commercial fungicide hymexazol (67.10 μg/mL). It was found that the substitutes in the 1,3,5-thiadiazine-2-thione and the 1,3,4-thiadiazole rings played a vital role in the antimicrobial activities of the title compounds. More active title compounds against phytopathogenic microorganisms might be obtained via further structural modification.

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Section: Introductionmentioning

confidence: 99%

Peer Review #1 of "Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group (v0.1)"

Cella¹

2019

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and further confirmed by the X-ray diffraction analysis of 8d. The antimicrobial activities of all the target compounds against Xanthomonas oryzae pv. oryzicola (Xoc), Xanthomonas oryzae pv. oryzae (Xoo), Rhizoctonia solani (Rs) and Fusarium graminearum (Fg) were evaluated. The in vitro antimicrobial bioassays indicated that some title compounds exhibited noteworthy antimicrobial effects against the above strains. Notably, the compound N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)-2-(5-methyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acetamide (8a) displayed obvious antibacterial effects against Xoc and Xoo at 100 µg/mL with the inhibition rates of 30% and 56%, respectively, which was better than the commercial bactericide thiodiazole-copper. In addition, the anti-Rs EC 50 value of 8a was 33.70 µg/mL, which was more effective than that of the commercial fungicide hymexazol (67.10 µg/mL).

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New series of 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazine thione (THTT) derivatives: Synthesis and potent antileishmanial activity

Cited by 22 publications

References 27 publications

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Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group

Peer Review #1 of "Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group (v0.1)"

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