Synthesis and Pharmacological Evaluation of Heterocycles from Benzocycloheptenones.

Venkateswarlu, P.; Vasireddy, Nageswara Rao

doi:10.1002/chin.200534045

Cited by 2 publications

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“…Compounds 1a-c were synthesized according to a published method (Baliah et al, 1948). Compounds 2a-c were prepared by methods used in previous reports (Balasubramanian et al, 2002, Venkateswarlu and Nageswara Rao, 2005, Sampath et al, 2006). Imidazolidin-2,4-dione derivatives 3a-c were prepared by cyclization of compounds 2a-c with ethyl chloroacetate in the presence of fused sodium acetate, following the method previously described (Jamal Abdul Nasser et al, 2008).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

Arif

Ahamed

Kumar

et al. 2019

Saudi Journal of Biological Sciences

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The objective of this study was to investigate brine shrimp cytotoxicity, larvicidal, nematicidal, and antifeedant activities of novel piperidin-connected 2-thioxo-imidazolidin-4-one derivatives. The activities of target compounds were compared with some naturally occurring (−)-pinidinol, hydantocidin, and positive controls. Target compounds were synthesized via cyclocondensation method. The compounds were synthesized and then characterized by infrared spectroscopy, 1 H NMR, 13 C NMR, mass spectral, and elemental analyses. Brine shrimp cytotoxicity assay was investigated using freshly hatched, free-swimming nauplii of Artemiasalina . Larvicidal screening was performed against urban mosquito larvae ( Culex quinquefasciatus ). Nematicidal activity was evaluated using juvenile nematodes of Meloidogyne javanica . Regarding antifeedant activity, marine-acclimated Oreochromis mossambicus fingerlings were used. Compounds 3a-c (piperidin-connected 2-thioxoimidazolidin-4-one) were found to be lethal to the second instar larvae of mosquito, which produced LD 50 values of 1.37, 6.66, 6.51 μg/mL, compared to compounds (−) pinidinol and hyantocidin LD 50 values of 18.28 and 22.11 μg/mL respectively. Compound 3a-c was found to kill 100% of fish fingerlings within 6 h at 20 µg/mL, with LD 50 values of 1.54, 1.79, 1.52 µg/mL, compared to compounds (−) pinidinol and hyantocidin with LD 50 values of 10.21 and 21.05 μg/mL respectively. Compound 3c with LD 50 value of 1.57 μg/mL demonstrated high nematicidal activity compared to compound 3a , 3b , (−) Pinidinol and Hyantocidin LD 50 values of 6.45, 2.42, 14.25, 26.30 μg/mL respectively. Therefore, the 2-thioxoimidazolidin-4-one with piperidin ring showed high potential cytotoxic, larvicidal, nematicidal, and antifeedent activities.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

Arif

Ahamed

Kumar

et al. 2019

Saudi Journal of Biological Sciences

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“…Acetylation of thiosemicarbazones 2(a-g) by acetic anhydride gave thiodiazolines derivatives 3(a-g) (scheme 1), (Venkateswarlu et al, 2005) and (Pawar et al, 2009). The main IR absorption bands of these products include stretching vibrations of two C=O and C=N bonds at (1695-1720 cm -1 ),(1572-1655 cm-1) and (1500-1617 cm -1 ) respectively (Pawar et al, 2009), in addition to a broad absorption at (2933-3280 cm -1 ) corresponding to N-H bond stretching.…”

Section: Theoretical Calculationmentioning

confidence: 99%

Synthesis of some Thiadiazoline Derivatives from 2- Phenyl Chroman-4-one

Raoof¹

2013

RJS

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2-Phenyl chroman-4-one 1(a-g) were synthesized by Pechmann condensation of proper phenol with cinnamic acid using poly phosphoric acid. Reactions of their derivatives with thiosemicarbazide were carried out using two methods, method A, using refluxing ethanol, gave low yield (17-20%). This method was modified to increase the yield using solvent free microwave irradiation technique, (method B), which improved the yield up to (30-40%). The treatment of these thiosemicabazones 2(a-g) with excess acetic anhydrid gave substituted thiadiazoline derivatives 3(a-g). The structure of these compounds was confirmed by IR, UV and NMR spectra in addition to their physical properties. On the other hand, the calculated values of the heat of formation and steric energy were established for compounds 2(a-g) and 3(a-g).

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Synthesis and Pharmacological Evaluation of Heterocycles from Benzocycloheptenones.

Cited by 2 publications

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Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

Cytotoxic, larvicidal, nematicidal, and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

Synthesis of some Thiadiazoline Derivatives from 2- Phenyl Chroman-4-one

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