N1‐allyl‐3‐substituted‐6,7‐dimethyl‐1,2‐dihydro‐2‐quinoxalinone as key intermediate for new acyclonucleosides and their regioisomer O‐analogues

Ali, Ibrahim A. I.; Fathalla, Walid

doi:10.1002/hc.20203

Cited by 17 publications

(10 citation statements)

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“…20 However a strong query still remains that is the development of simple, mild and efficient methods for preparation of quinazoline derivatives linked to amino acid residues by a spacer and the evaluation of their biological activities. In view of these facts and in continuation of our efforts in studing the chemoselective reactions of heterocyclic amides [21][22][23] and thioamides, 20,[24][25][26][27][28][29][30][31][32][33][34][35][36][37] we found interesting to synthesize a series of quinazoline derivatives linked to amino acids by a spacer. Here in we wish to report a novel synthesis of 3-arylquinazoline-2,4-dione and use this precursor in the synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-2-ylthio) acetohydrazide 6.

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Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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“…Thus, a protocol of using allyl bromide as an alkylating agent and sodium hydride in dimethylformamide at 100 °C. The dihydroxylation of N and O alkyl derivatives and compound, was performed with AD-mix β in a mixture t-butanol-water [86]. a) Allyl bromide, NaH, DMF, 100 °C b) AD-mixβ.…”

Section: Reactivity Of Quinoxaline Derivativesmentioning

confidence: 99%

Synthetic Methods and Exploring Biological Potential of Various Substituted Quinoxalin-2-one Derivatives

2016

European Reviews of Chemical Research

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Substituted quinoxaline have considerable interest in chemistry, biology and pharmacology. Quinoxaline derivatives are capable with variety of biological activities and possess different biological activities, of which the most potent are anti-microbial, analgesic and anti-inflammatory activities. It facilitated the researchers to develop various methods for their synthesis and their applications. In this review represented different methods of synthesis, reactivity and various biological activities of quinoxaline derivatives.Keywords: Quinoxaline, reactivity, biological activities, synthetic methods. IntroductionQuinoxaline and its derivatives are important nitrogen containing heterocyclic compounds of various biologically properties. Quinoxaline and its derivatives are mostly of synthetic origin. Substituted quinoxalines are an important class of benzoheterocycles, which constitute the building blocks of wide range of pharmacologically active compounds having antibacterial [1][2][3][4] [15] activities. The quinoxaline is described as a bioisoster of quinoline, naphthalene, benzothiophene and other aromatic rings such as pyridine and pyrazine. Because of the similarity between some antitubercular drugs and quinoxaline, as well as the presence of the quinoxaline moiety in some broad spectrum antibiotics, it was hoped that quinoxaline analogs would exhibit antitubercular activity [16]. The quinoxaline antibiotics are agents of bicyclic desipeptide antibiotic that have been reported activity against gram-positive bacteria and certain tumors and to inhibit RNA synthesis [17]. Quinoxaline has also been used in reactive dyes and pigments, azo dyes, fluroscein dyes and it also forms a part of certain antibiotics. Quinoxaline m.p. 29-30ºC and is miscible with water. It is weakly basic (pka 0.56) and thus considerably weaker base than the isomeric diazonapthalenes namely cinnoline (pka 2.42), pthalizine (pka 3.47) or quinazoline (pka 1.95). 2-Hydroxy-but not 2-amino quinoxaline exist in tautomeric forms.

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“…Recently, Ali and Fathalla [25] have reported the regioselective alkylation of quinoxalines with allyl bromide in the presence of NaH to give a mixture of O-and N-allyl-substituted quinoxalines 3 (27-33%) and __________________________________________________________________________________________…”

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confidence: 98%

“…Furthermore, 1'-CH 2 proton at δ H 4.16-4.25 showed 3 J C,H couplings with C=O at δ C 158.2-154.1, and 2 J C,H couplings with C-2' at δ C 26.0. The quinoxaline carbon atoms were fully analyzed and are in agreement with those of the known derivatives prepared previously [25]. The structures of the O-alkyl analogs 17-22 were confirmed from the NMR and mass spectra.…”

mentioning

confidence: 99%

“…These studies prompted us to use the 1,2-dihydroquinoxalone as nucleobase carrying alkyl side chains at N and O atoms, since some quinoxaline derivatives showed a remarkable biological activity [15,16]. The pharmacological applications of quinoxalines include their use as angiotension II receptor antagonists [17], N-methyl-D-aspartate (NMDA) antagonists [18], anti-inflammatory [19], antidepressant-tranquilizing [20, 21], antitumor agents [22,23], as well as the agents against hepatitis B virus (HBV) [24].Recently, Ali and Fathalla [25] have reported the regioselective alkylation of quinoxalines with allyl bromide in the presence of NaH to give a mixture of O-and N-allyl-substituted quinoxalines 3 (27-33%) and __________________________________________________________________________________________ …”

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confidence: 99%

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Synthesis and anti-HIV activity of new homo acyclic nucleosides, 1-(pent-4-enyl)quinoxalin-2-ones and 2-(pent-4-enyloxy)quinoxalines

Ali

Al-Masoudi

Hassan

et al. 2007

Chem Heterocycl Comp

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A series of acyclonucleosides 6,7-disubstituted 1- (pent-4-enyl)quinoxalin-2-one derivatives and the O-analogs were synthesized by a one-step condensation of the corresponding quinoxaline bases with 5-bromo-1-pentene.The acyclonucleosides prepared were assayed against HIV-1 and HIV-2 in quinoxaline showed inhibition of HIV-1 with EC 50 value of 0.22 ± 0.08 µg/ml and a therapeutic index of 13. This means that it was cytotoxic to MT-4 cells at CC 50 of 2.6 ± 0.1 µg/ml.The use of acyclonucleoside analogs as antiviral chemotherapeutic agents has stimulated extensive research in the synthesis of this class of compounds [1][2][3][4]. The discovery of acyclovir (Zovirax ® ) [5, 6] as a potent antiherpetic drug [7-9] was followed by a great number of chemical analogs of acyclovir such as (RS)-9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine (HBG) (1), 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine (DHPG) 2 [10, 11], 9-(2-phosphonylmethoxyethyl)adenine (PMEA) and (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA) [12] derivatives. Structure−activity relationship studies have shown that the side chains of acyclonucleosides play a crucial role in the interaction of the acyclonucleosides with their antiviral target enzymes [13] (phosphorylation). The orientation of the heterocyclic base about the glycosidic bond in nucleosides is an important conformational parameter, and has been clearly delineated in a variety of enzymatic reactions [14]. These studies prompted us to use the 1,2-dihydroquinoxalone as nucleobase carrying alkyl side chains at N and O atoms, since some quinoxaline derivatives showed a remarkable biological activity [15,16]. The pharmacological applications of quinoxalines include their use as angiotension II receptor antagonists [17], N-methyl-D-aspartate (NMDA) antagonists [18], anti-inflammatory [19], antidepressant-tranquilizing [20, 21], antitumor agents [22,23], as well as the agents against hepatitis B virus (HBV) [24].Recently, Ali and Fathalla [25] have reported the regioselective alkylation of quinoxalines with allyl bromide in the presence of NaH to give a mixture of O-and N-allyl-substituted quinoxalines 3 (27-33%) and __________________________________________________________________________________________

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N¹‐allyl‐3‐substituted‐6,7‐dimethyl‐1,2‐dihydro‐2‐quinoxalinone as key intermediate for new acyclonucleosides and their regioisomer O‐analogues

Cited by 17 publications

References 22 publications

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Synthetic Methods and Exploring Biological Potential of Various Substituted Quinoxalin-2-one Derivatives

Synthesis and anti-HIV activity of new homo acyclic nucleosides, 1-(pent-4-enyl)quinoxalin-2-ones and 2-(pent-4-enyloxy)quinoxalines

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