Reaction of aromatic o-diamines with isatins. 2. 2,3-diaminonaphthalene

Drushlyak, A. G.; Иващенко, А. В.; Титов, В. В.

doi:10.1007/bf00503611

Cited by 4 publications

(2 citation statements)

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“…Compound 1-4 was prepared by condensation of 5-Substituted-1-methyl-1H-Indole-2,3-dione and 2,3-diaminonaphthalene in acetic acid. Preparation of BIQCH 3 (1), BIQCH 3 Br (3) and BIQCH 3 NO 2 (4) are reported in literature [21,22]. However BIQCH 3 CH 3 (2) is not reported and all of these compounds are confirmed by FT-IR, 1 H NMR, 13 C NMR, MASS spectra and elemental analysis.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…Benz [g]indolo [2,3-b]quinoxalines is a built in donor-acceptor chromophores as it contain the electron rich indole unit fused with electron deficient quinoxaline moiety, however they are reported in literature [21,22] and are used in medicinal chemistry as an antiviral and anticancer agents [23,24]. Considering the importance of indolo [2,3-b]quinoxalines in material sciences it was decided to investigate the optoelectronic and thermal properties of Benz[g]indolo [2,3-b]quinoxalines.…”

Section: Introductionmentioning

confidence: 99%

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Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

Shaikh¹,

Sharma²,

Kamble

2015

Can. Chem. Trans.

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Abstract:In this work, 5-methyl-5H-Benz[g]indolo [2,3-b]quinoxaline (BIQCH 3 ) and its derivatives were prepared in good yield by condensing 5-Substituted-1-methyl-1H-Indole-2,3-dione and 2,3-diaminonaphthalene in glacial acetic acid. The structure of BIQCH 3 and its derivatives were confirmed using FT−IR, 1 H NMR, 13 C NMR, Mass spectra and elemental analysis. The photophysical and electrochemical studies of BIQCH 3 and its derivatives were studied by UV-Visible spectroscopy, fluorescence spectroscopy and cyclic voltammetry respectively. The optical energy band gap of BIQCH 3 and its derivatives lies in the range of 2.53 ̶ 2.58 eV. Thermal analysis of BIQCH 3 and its derivative were studied by Thermo Gravimetric Analysis (TGA) and Differential Thermal Analysis (DTA).

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

Shaikh¹,

Sharma²,

Kamble

2015

Can. Chem. Trans.

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The interaction of ellipticine derivatives with nucleic acids studied by optical and ¹H‐nmr spectroscopy: Effect of size of the heterocyclic ring system

et al. 1994

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The DNA interaction of derivatives of ellipticine with heterocyclic ring systems with three, four, or five rings and a dimethylaminoethyl side chain was studied. Optical spectroscopy of drug complexes with calf thymus DNA, poly[(dA-dT).(dA-dT)], or poly[(dG-dC).(dG-dC)] showed a 10 nm bathochromic shift of the light absorption bands of the pentacyclic and tetracyclic compounds upon binding to the nucleic acids, which indicates binding by intercalation. For the tricyclic compound a smaller shift of 1-3 nm was observed upon binding to the nucleic acids. Flow linear dichroism studies show that the geometry of all complexes is consistent with intercalation of the ring system, except for the DNA and poly[(dG-dC).(dG-dC)] complexes of the tricyclic compound, where the average angle between the drug molecular plane and the DNA helix axis was found to be 65 degrees. One-dimensional 1H-nmr spectroscopy was used to study complexes between d(CGCGATCGCG)2 and the tricyclic and pentacyclic compounds. The results on the pentacyclic compound show nonselective broadening due to intermediate chemical exchange of most oligonucleotide resonances upon drug binding. The imino proton resonances are in slow chemical exchange, and new resonances with upfield shifts approaching 1 ppm appear upon drug binding, which supports intercalative binding of the pentacyclic compound. The results on the tricyclic compound show more rapid binding kinetics and very selective broadening of resonances. The data suggest that the tricyclic compound is in an equilibrium between intercalation and minor groove binding, with a preference to bind close to the AT base pairs with the side chain residing in the minor groove.

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Derivatives of 1,2-diaminoimidazole in reactions with acetylarenes

Orlov

Papiashvili

Povstyanoi

et al. 1984

Chem Heterocycl Compd

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Reaction of aromatic o-diamines with isatins. 2. 2,3-diaminonaphthalene

Cited by 4 publications

References 3 publications

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

The interaction of ellipticine derivatives with nucleic acids studied by optical and ¹H‐nmr spectroscopy: Effect of size of the heterocyclic ring system

Derivatives of 1,2-diaminoimidazole in reactions with acetylarenes

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Reaction of aromatic o-diamines with isatins. 2. 2,3-diaminonaphthalene

Cited by 4 publications

References 3 publications

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

Photophysical, Electrochemical and Thermal Studies of 5-methyl-5H-Benz[g]indolo[2,3-b]quinoxaline Derivatives: Green and Yellow Fluorescent Materials

The interaction of ellipticine derivatives with nucleic acids studied by optical and 1H‐nmr spectroscopy: Effect of size of the heterocyclic ring system

Derivatives of 1,2-diaminoimidazole in reactions with acetylarenes

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The interaction of ellipticine derivatives with nucleic acids studied by optical and ¹H‐nmr spectroscopy: Effect of size of the heterocyclic ring system