Studies on Biological Activity of Cyclic Imide Compounds Part II

Fujinami, Akira; Ozaki, Tatsuo; Nodera, Katsuji; Tanaka, Kuniji

doi:10.1271/bbb1961.36.318

Cited by 69 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Both groups of molecules are important compounds in biological chemistry, biotechnology, and organic synthesis. − Succinimide and its derivatives are used pharmaceutically as analgesics and anticonvulsants. − In industry, succinimides are also used as lubricants in oils, emulsion explosives, and corrosion inhibitors . They also display antifungal and antimicrobial properties, and they even have activity as insecticides . In these applications, substitution at the N atom is employed, making the structural consequences of N - substitution an important determiner of the overall molecular shape.…”

Section: Introductionmentioning

confidence: 99%

A Tale of Two Tails: Rotational Spectroscopy of N-Ethyl Maleimide and N-Ethyl Succinimide

York,

Sorrells,

Dim

et al. 2024

J. Phys. Chem. A

View full text Add to dashboard Cite

Broadband microwave spectra of N-ethyl maleimide (NEM) and Nethyl succinimide (NES) have been recorded using chirped pulse Fourier transform microwave spectroscopy in the K a -band (26.5−40 GHz). The spectra for both molecules were fit to a Watson A-reduced Hamiltonian in the I r representation to obtain best fit experimental rotational constants (NEM: A 0 = 2143.1988(29), B 0 = 1868.7333(22), C 0 = 1082.98458(36); NES: A 0 = 2061.47756(14), B 0 = 1791.73517(12), C 0 = 1050.31263( 11)), centrifugal distortion constants, and nuclear quadrupole coupling constants. While the heavy atoms of the fivemembered ring of both molecules are planar, the ethyl chain has its terminal methyl group perpendicular to the ring. Along the relaxed potential energy curve for the ethyl dihedral angle (θ 1 = C(6)−C(5)−N−C(4)), the ethyl group experiences significant steric strain when it is in the plane of the ring, associated with the interaction of the ethyl group with the two carbonyl oxygens. This leads to calculated barriers of θ 1 = 1469 cm −1 and θ 1 = 1680 cm −1 in N-ethyl maleimide and N-ethyl succinimide, respectively.

show abstract

Section: Introductionmentioning

confidence: 99%

A Tale of Two Tails: Rotational Spectroscopy of N-Ethyl Maleimide and N-Ethyl Succinimide

York,

Sorrells,

Dim

et al. 2024

J. Phys. Chem. A

View full text Add to dashboard Cite

show abstract

“…Another moiety worth investigation is succinimide, because N -phenylsuccinimides are regarded as some of the most efficacious agricultural fungicides [29–30]. They have also been shown to be selective nephrotoxic compounds [31–32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

Maftei

Fodor²,

Jones³

et al. 2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryTaking into consideration the biological activity of the only natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were synthesized starting from 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) in two steps by isolating the intermediates 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobutanoic acid (3) and (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic acid (6). The two natural product analogs 4 and 7 were then tested for antitumor activity toward a panel of 11 cell lines in vitro by using a monolayer cell-survival and proliferation assay. Compound 7 was the most potent and exhibited a mean IC50 value of approximately 9.4 µM. Aniline 1 was synthesized by two routes in one-pot reactions starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography.

show abstract

Fungicides, Dicarboximides

Leroux¹

2002

Encyclopedia of Agrochemicals

View full text Add to dashboard Cite

The dicarboximide fungicides are in fact cyclic imides substituted on the nitrogen atom by a 3,5‐dichlorophenyl group. They can be used against various Ascomycetes (e.g., Alternaria , Botrytis , Monilinia , Sclerotinia ) and Basidiomycetes (e.g., Rhizoctonia ). Under field conditions, their activity against fungal pathogens is mainly preventive. Their target site could be a histidine protein kinase–involved fungal osmoregulation. In field strains and laboratory mutants of Botrytis cinerea , dicarboximide resistance seems to be determined by mutations in the gene encoding this kinase. The metabolism of these dicarboximides generally involves the cleavage of the cyclic imide.

show abstract

Studies on Biological Activity of Cyclic Imide Compounds Part II

Cited by 69 publications

References 0 publications

A Tale of Two Tails: Rotational Spectroscopy of N-Ethyl Maleimide and N-Ethyl Succinimide

A Tale of Two Tails: Rotational Spectroscopy of N-Ethyl Maleimide and N-Ethyl Succinimide

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

Fungicides, Dicarboximides

Contact Info

Product

Resources

About