Formation of 1,2-dihydroquinazolin-4(3H)-ones. Reinvestigation of a recently reported 1,3,-4-benzotriazepine synthesis

Fülöp, Ferenc; Simeonov, Mario F.; Pihlaja, Kalevi

doi:10.1016/s0040-4020(01)89014-1

Cited by 32 publications

(11 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Structure IV, formed as a result of that rearrangement, is not stable and, after translocation of the hydrogen atom from the carbonyl oxygen atom, transforms into compound 17, which is the product of this reaction chain. Another sequence of intermediate compounds leading to formation of the product is also plausible (as previously reported by N. P. Peet and S. Sunder [6] ; F. Fülöp [11] ).…”

Section: Resultssupporting

confidence: 67%

See 1 more Smart Citation

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Ryng¹,

Zimecki

Fedorowicz

et al. 2001

Arch. Pharm. Pharm. Med. Chem.

View full text Add to dashboard Cite

Section: Resultssupporting

confidence: 67%

“…Fülöp and co-workers recently demonstrated [11] that the reactions of o-aminobenzoylhydrazide 5 with one equivalent of benzylideneanilines or aldehydes gave product 1. In the reaction, one mole of 5 and two moles of the Schiff's base or aldehyde resulted in compound 3.…”

Section: Introductionmentioning

confidence: 99%

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Ryng¹,

Zimecki

Fedorowicz

et al. 2001

Arch. Pharm. Pharm. Med. Chem.

View full text Add to dashboard Cite

“…Compound 1 and the intermediate compounds (2a-f) were prepared according to the reported methods [26,27]. Their properties were as follows: Compounds 3a-f were prepared with the same procedure.…”

Section: Synthesis Of 6-mentioning

confidence: 99%

Comparative Interactions of Dihydroquinazolin Derivatives with Human Serum Albumin Observed via Multiple Spectroscopy

et al. 2017

View full text Add to dashboard Cite

Abstract:The interactions of dihydroquinazolines with human serum albumin (HSA) were studied in pH 7.4 aqueous solution via fluorescence, circular dichroism (CD) and Fourier transform infrared (FTIR) spectroscopic techniques. In this work, 6-chloro-1-(3,3-dimethyl-butanoyl)-2-(un)substitutedphenyl-2,3-dihydroquinazolin-4(1H)-one (PDQL) derivatives were designed and synthesized to study the impact of five similar substituents (methyl, methoxy, cyano, trifluoromethyl and isopropyl) on the interactions between PDQL and HSA using a comparative methodology. The results revealed that PDQL quenched the intrinsic fluorescence of HSA through a static quenching process. Displacement experiments with site-specific markers revealed that PDQL binds to HSA at site II (subdomain IIIA) and that there may be only one binding site for PDQL on HSA. The thermodynamic parameters indicated that hydrophobic interactions mainly drove the interactions between PDQL and HSA. The substitution using five similar groups in the benzene ring could increase the interactions between PDQL and HSA to some extent through the van der Waals force or hydrogen bond effects in the proper temperature range. Isopropyl substitution could particularly enhance the binding affinity, as observed via comparative studies.

show abstract

“…Compound 1 and compounds 2a-d were prepared according to the reported methods [47,48]. Their properties were as follows: For the preparation of compounds 3a-d, the corresponding compound 2 (3 mmol) in anhydrous tetrahydrofuran (30 mL) was cooled to 0 • C with an ice bath, and sodium hydride (3.6 mmol) was added.…”

Section: Fourier Transform Infrared (Ft-ir) Measurementsmentioning

confidence: 99%

Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy

Zhu

et al. 2016

Molecules

View full text Add to dashboard Cite

Abstract:In the present study, 3-(fluorobenzylideneamino)-6-chloro-1-(3,3-dimethylbutanoyl)-phenyl-2,3-dihydroquinazolin-4(1H)-one (FDQL) derivatives have been designed and synthesized to study the interaction between fluorine substituted dihydroquinazoline derivatives with human serum albumin (HSA) using fluorescence, circular dichroism and Fourier transform infrared spectroscopy. The results indicated that the FDQL could bind to HSA, induce conformation and the secondary structure changes of HSA, and quench the intrinsic fluorescence of HSA through a static quenching mechanism. The thermodynamic parameters, ∆H, ∆S, and ∆G, calculated at different temperatures, revealed that the binding was through spontaneous and hydrophobic forces and thus played major roles in the association. Based on the number of binding sites, it was considered that one molecule of FDQL could bind to a single site of HSA. Site marker competition experiments indicated that the reactive site of HSA to FDQL mainly located in site II (subdomain IIIA). The substitution by fluorine in the benzene ring could increase the interactions between FDQL and HSA to some extent in the proper temperature range through hydrophobic effect, and the substitution at meta-position enhanced the affinity greater than that at para-and ortho-positions.

show abstract

Formation of 1,2-dihydroquinazolin-4(3H)-ones. Reinvestigation of a recently reported 1,3,-4-benzotriazepine synthesis

Cited by 32 publications

References 11 publications

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Reactions of 5-Amino-3-methylisoxazole-4-carboxylic Acid Hydrazide with Carbonyl Compounds: Immunological Activity and QSAR Studies of Products

Comparative Interactions of Dihydroquinazolin Derivatives with Human Serum Albumin Observed via Multiple Spectroscopy

Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy

Contact Info

Product

Resources

About