Design, synthesis, structure elucidation, and biological activities of 3-(substituted amino)-1-(pyridin-4-yl)propenones and 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane hybrids

Kalita, Utpalparna; Kaping, Shunan; Nongkynrih, Revinus; Boiss, Ivee; Singha, Laishram Indira; Vishwakarma, Jai N.

doi:10.1007/s00706-017-2020-y

Cited by 5 publications

(2 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…-Enaminones may be used in the synthesis of many bioactive molecules with a heterocyclic unit. Enaminones as intermediates are responsible for a wide range of therapeutic agents from both natural and synthetic sources including taxol, ISSN 2056-9890 anticonvulsants, anti-inflammatories, and duocarmycin, and consequently have been the subject of numerous structural bioactivity investigations in recent times (Misra et al, 2008;Greenhill, 1977;Boger et al, 1989;Eddington et al, 2003;Stoltz et al, 2016;Jerach & Elassar, 2015;Kalita et al, 2017). In spite of the breadth of research related to the biological properties of enaminones, recent research also indicates that enaminones, particularly the cyclic 3-(phenylamino)-2-cyclohexen-1-one (PACO), contain spectroscopic signatures of intramolecular charge transfer (ICT), making cyclic enaminones ideal components for molecules that mimic natural photosynthetic energy and electron transfer (Lue & Greenhill, 1996).…”

Section: Chemical Contextmentioning

confidence: 99%

Syntheses and structures of two benzoyl amides: 2-chloro-4-ethoxy-3,5-dimethoxy-N-(3-oxocyclohex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-4-ethoxy-3,5-dimethoxybenzamide

2021

View full text Add to dashboard Cite

The first title benzoyl amide, C17H20ClNO5 (3a), crystallizes in the monoclinic space group P21/c with Z = 4 and the second, C19H24ClNO5 (3b), also crystallizes in P21/c with Z = 8 (Z′ = 2), thus there are two independent molecules in the asymmetric unit. In 3a, the phenyl ring makes a dihedral angle of 50.8 (3)° with the amide moiety with the C=O group on the same side of the molecule as the C—Cl group. One methoxy group is almost in the plane of the benzene ring, while the ethoxy and other methoxy substituent are arranged on opposite sides of the ring with the ethoxy group occupying the same side of the ring as the C=O group in the amide moiety. For one of the two molecules in 3b, both the amide and 5,5-dimethyl-3-oxocyclohex-1-en-1-yl moieties are disordered over two sets of sites with occupancies of 0.551 (2)/0.449 (2) with the major difference between the two conformers being due to the conformation adopted by the cyclohex-2-en-1-one ring. The three molecules in 3b (i.e., the undisordered molecule and the two disorder components) differ in the arrangement of the subsituents on the phenyl ring and the conformation adopted by their 5,5-dimethyl-3-oxocyclohex-1-en-1-yl moieties. In the crystal of 3a, N—H...O hydrogen bonds link the molecules into a zigzag chain propagating in the [001] direction. For 3b a combination of C—H...O and N—H...O intermolecular interactions link the molecules into a zigzag ribbon propagating in the [001] direction.

show abstract

Section: Chemical Contextmentioning

confidence: 99%

Syntheses and structures of two benzoyl amides: 2-chloro-4-ethoxy-3,5-dimethoxy-N-(3-oxocyclohex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-4-ethoxy-3,5-dimethoxybenzamide

2021

View full text Add to dashboard Cite

show abstract

“…In another study done in 2017, ferrocenylmethylidene and arylidene substituted adamantane ring based compounds as potential anticancer properties were synthesized [8]. In another study, biologically active adamantyl hybrid compounds were synthesized [9]. Recently, adamantyl derivative studies have been carried out with important biological properties such as cytotoxic, selective cannabinoid type 2 receptor agonists, interleukin inhibitor, antitubercular, photoswitchable receptor antagonist, antimicrobial and antitumor activities [10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine

Doğan

Sellitepe²,

Kahveci³

2019

Hacettepe Journal of Biology and Chemistry

View full text Add to dashboard Cite

B u çalışmada, 1-adamantil amin bileşiğinin 4 farklı ester etoksikarbonil hidrazon türevi ile reaksiyonu incelenmiştir. İlk olarak, iminoester hidroklorür türevleri Pinner yöntemine göre sentezlendi. Daha sonra, ester etoksikarbonil hidrazon türevi bileşiklerinin sentezlenmesi için etil karbazat ile reaksiyona sokuldu. Son basamakta, 3-sübstitüe-4-adamantil-1,2,4triazol-5-on türevlerinin sentezlenmesi amaçlandı, ester etoksikarbonil hidrazin türevli bileşikler 1-adamantil amin ile bir yağ banyosunda kuru kuruya ısıtıldı. Ancak, IR ve ¹H-NMR analizleri ile halkanın kapanmadığı anlaşıldı ve etil N-(adamantilkarbamoil)alkilkarbohidrazonoat türevi bileşiklerin stabil ve orijinal bileşikler olarak sentezlendiği gözlenmiştir. Sentezlenen bileşiklerin yapısı, IR, ¹H-NMR, 13 C-NMR spektrumları ve LC/MS analizi gibi spektroskopik yöntemlerle kanıtlandı.

show abstract

Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones

et al. 2021

View full text Add to dashboard Cite

Design, synthesis, structure elucidation, and biological activities of 3-(substituted amino)-1-(pyridin-4-yl)propenones and 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane hybrids

Cited by 5 publications

References 48 publications

Syntheses and structures of two benzoyl amides: 2-chloro-4-ethoxy-3,5-dimethoxy-N-(3-oxocyclohex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-4-ethoxy-3,5-dimethoxybenzamide

Syntheses and structures of two benzoyl amides: 2-chloro-4-ethoxy-3,5-dimethoxy-N-(3-oxocyclohex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)-4-ethoxy-3,5-dimethoxybenzamide

Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine

Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones

Contact Info

Product

Resources

About