Synthesis of Thiazolidin‐4‐ones from Substituted (Ylidene)hydrazinecarbothioamides and Dimethyl Acetylenedicarboxylate

Hassan, Alaa A.; Aly, Ashraf A.; El‐Shaieb, Kamal M.; Bedair, Tarek M.; Bräse, Stefan; Brown, Alan B.

doi:10.1002/jhet.1642

Cited by 12 publications

(5 citation statements)

References 29 publications

(25 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The signal of the protons of the -OCH 3 group resonates in the form of a singlet at 3.76 ppm. The signal of N=CH shows a doublet at δH = 7.87-7.90 ppm because of the anisotropy of the N (sp 2 ) atom, 15 The 1 H-NMR spectrum of the thiosemicarbazone shows two doublets at δH = 6.97-7.05 ppm because of (CH=CH) (Fig. S2 from the supplementary materials SI), whereas N-H thiourea protons are found at 9.87 and 11.84 ppm for N-H adjacent to the monosubstituted phenyl ring and for N-H adjacent to the CH=N moiety, respectively.…”

Section: H-nmr and 13 C-nmr Spectramentioning

confidence: 99%

Synthesis and characterization of novel thiosemicarbazide for nonlinear optical applications: combined experimental and theoretical study

HADJI,

BENMOHAMMED,

MOUCHAAL

et al. 2023

Rev.Roum.Chim.

View full text Add to dashboard Cite

(E)-4-(4-methoxyphenyl)-1-((E)-3(2nitrophenyl) allylidene) thiosemicarbazide was synthesised and screened for nonlinear optical properties. The novel compound has been characterized by infrared spectroscopy, 1H and 13C nuclear magnetic resonance. The experimental and theoretical optical gap energy is obtained using the Tauc method and density functional theory and has been estimated to be around 2.72 and 2.69 eV, respectively. The synthesized thiosemicarbazide exhibits efficiency hyper-Rayleigh scattering hyperpolarizability is calculated to be 6794.51 a.u. at the PBE0 functional. A direct relationship of the hyper-Rayleigh scattering hyperpolarizability with the optical band gap and between the hyper-Rayleigh scattering hyperpolarizability and electric field-induced second harmonic generation is found. The study showed the potential of the novel thiosemicarbazide as nonlinear optical candidates.

show abstract

Section: H-nmr and 13 C-nmr Spectramentioning

confidence: 99%

Synthesis and characterization of novel thiosemicarbazide for nonlinear optical applications: combined experimental and theoretical study

HADJI,

BENMOHAMMED,

MOUCHAAL

et al. 2023

Rev.Roum.Chim.

View full text Add to dashboard Cite

show abstract

“…were prepared by the reaction of 4-substituted thiosemicarbazide with the proper aldehyde according to the published procedures in literature (2a [68], 2b [69], 2c [70], 2d [68] and 2e [70]).…”

Section: Starting Materials-substituted Alkenylidene-hydrazinecarbothmentioning

confidence: 99%

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

Hassan

Aly

Mohamed

et al. 2019

Bioorganic Chemistry

Self Cite

View full text Add to dashboard Cite

A large number of natural products containing the propellane scaffold have been reported to exhibit cytotoxicity against several cancers; however, their mechanism of action is still unknown. Anticancer drugs targeting DNA are mainly composed of small planar molecule/s that can interact with the DNA helix, causing DNA malfunction and cell death. The aim of this study was to design and synthesize propellane derivatives that can act as DNA intercalators and/or groove binders. The unique structure of the propellane derivatives and their ability to display planar ligands with numerous possible geometries, renders them potential starting points to design new drugs targeting DNA in cancer cells. New substituted furo-imidazo[3.3.3]propellanes were synthesized via the reaction of substituted alkenylidene-hydrazinecarbothioamides with 2-(1,3-dioxo-2,3dihydro-1H-2-ylidene) propanedinitrile in tetrahydrofuran at room temperature. The structures of the products were confirmed by a combination of elemental analysis, NMR, ESI-MS, IR and single crystal X-ray analysis. Interestingly, 5c, 5d and 5f showed an ability to interact with Calf Thymus DNA (CT-DNA). Their DNA-binding mode was investigated using a combination of absorption spectroscopy, DNA melting, viscosity, CD spectroscopy measurements, as well as competitive binding studies with several dyes. Their cytotoxicity was evaluated against the NCI-60 panel of cancer cell lines. 5c, 5d and 5f exhibited similar anti-proliferative activity against the A549 non-small cell lung cancer (NSCLC) cell line. Further mechanistic studies revealed their ability to induce DNA damage in the A549 cell line, as well as apoptosis, evidenced by elevated *

show abstract

“…Various substituted alkenylidene hydrazinecarbothioamides 6a-e were prepared by the reaction of 4-substituted hydrazinecarbothioamides with the proper aldehyde according to the published procedures in literature; 6b [28] 6c [29] and 6e [24].…”

Section: Starting Materialsmentioning

confidence: 99%

Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds

et al. 2019

Self Cite

View full text Add to dashboard Cite

The reaction between N-substituted alkenylidene hydrazinecarbothioamides and two molar amounts of ethene-1,1,2,2-tetracarbonitrile (TCNE) in anhydrous THF at room temperature without using any catalyst affords (Z)-4amino-3-(substituted amino)-2-(substituted imino)-2,3-dihydrothiazole-5-carbonitrile and (Z)-(4-amino-5-cyano-3substitued thiazol-2(3H)-ylidene)carbonohydrazonoyl dicyanide. Rationales for these transformations are presented.The structures of the obtained products were confirmed via single crystal X-ray analyses.

show abstract

Synthesis of Thiazolidin‐4‐ones from Substituted (Ylidene)hydrazinecarbothioamides and Dimethyl Acetylenedicarboxylate

Abstract: Conjugated substituted (ylidene)hydrazinecarbothioamides react in high yield with dimethyl acetylenedicarboxylate to give substituted [(ylidene)hydrazono)‐4‐oxothiazolidin‐5‐ylidene]acetates; several mechanistic options involving nucleophilic interaction are presented.

Cited by 12 publications

References 29 publications

Synthesis and characterization of novel thiosemicarbazide for nonlinear optical applications: combined experimental and theoretical study

Synthesis and characterization of novel thiosemicarbazide for nonlinear optical applications: combined experimental and theoretical study

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds

Contact Info

Product

Resources

About