2,5-Benzodiazocines and intermediates

Sulkowski, Theodore S.; Wille, M A; Mascitti, A.; Diebold, James L.

doi:10.1021/jo01282a022

Cited by 26 publications

(9 citation statements)

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“…The imidazole ring of substituted isoindolo[2,1-a]-benzimidazol-11-ones 42 can be cleaved as a result of hydrogenolysis. The obtained 2-(2-aminophenyl)phthalimidines 74 can then be used for the production of 2-(2-aminophenyl)isoindolines 75 [88]. Schemes for the decomposition were proposed using the extended Hückel method [94].…”

Section: Nitrationmentioning

confidence: 99%

“…Reactions of o-Arylene diamines with o-Aroyl-and o-Acetylbenzoic Acids. The condensation of o-acylbenzoic acids [45-51] with the diamine 1a, leading to substituted isoindolobenzimidazoles 42, , where X = p(m)-Cl, Br, F, CF 3 , Me, Et, OMe, OEt 1aIn the case of o-aroylcyclohexanecarboxylic acids the corresponding 4b-aryl-substituted 1,2,3,4-tetrahydroisoindolobenzimidazolones 44a,b are formed with yields of ~50%[52][53][54]…”

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confidence: 99%

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11H-isoindolo[2,1-a]benzimidazoles (Review)

Lyaskovskyy

Voitenko

Ковтуненко

2007

Chem Heterocycl Compd

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Section: Nitrationmentioning

confidence: 99%

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confidence: 99%

11H-isoindolo[2,1-a]benzimidazoles (Review)

Lyaskovskyy

Voitenko

Ковтуненко

2007

Chem Heterocycl Compd

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“…Further oxidation to the sulfone 31 completely inactivates the molecule. Replacement of the sulfur by O, NH, and CH2 32-34 as well as ring enlargement of the same series by a methylene group yielded the less active 2,3-dihydrooxazolo[2,3-a] isoindol-5(9bfl)-one (32 (36), l,2,3,10b-tetrahydropyrimido[2,l-a]isoindol-6(2H)-one (37), and 1,2,3,-10b-tetrahydropyrido[2,l-a]isoindol-6(2H)-one (38). In general, five-membered rings were more potent than sixmembered rings, and the antiviral activity decreased in the series S > O > CH2 > NH.…”

Section: Chemistrymentioning

confidence: 99%

Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity

Mertens¹,

Zilch²,

König³

et al. 1993

J. Med. Chem.

196

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A series of substituted 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds 1-73 were synthesized and evaluated for their ability to inhibit reverse transcriptase (RT) of the human immune deficiency virus 1 (HIV-1) and replication of HIV-1 in MT2 cells. The antiviral activity of these compounds depends on the stereoselective configuration of the substituent in position 9b. Structure-activity studies were done within these series of compounds to determine the optimum substituents for antiviral activity. The most potent inhibitors were found in the class of 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones bearing a phenyl ring system in position 9b optionally substituted with one or two methyl groups or a chlorine atom in position 8. The most active analogues (R)-(+)-1, (R)-(+)-6, (R)-(+)-13, (R)-(+)-26, and (R)-(+)-53 inhibit the HIV-1 RT with an IC50 between 16 and 300 nM and an IC50 between 10 and 392 nM in MT2 cells, respectively.

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“…[4]. Also, they are useful intermediates in synthetic organic chemistry, particularly in the amplification of imidazo[2,1-a]isoindolol-based anorectics, [2,5,6]central nervous system (CNS) stimulants [7,8] and antidepressants, [9] respectively. This class of compounds has also confirmed to be highly effective plant growth regulating agents [10] with effects on the plant budding process [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

A Combined Experiment and Computation Study of the Fused Polycyclic Benzimidazole Derivatives

2014

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Novel fused polycyclic benzimidazole derivatives were synthesized from dimethyl 4,5-diaminophthalate/dimethyl 3,4-diaminophthalate with aromatic anhydride (a-b) by condensation. The UV-Visible absorption and fluorescence emission spectra of the dyes were studied in solvents of differing polarity. The dyes were characterized by the spectral analysis. Density Functional Theory computations have been used to derive more understanding of structural, molecular, electronic and photophysical parameters of the push-pull dyes. The computed absorption wavelength values were observed to be in good agreement with the experimental results. The second order hyperpolarizability (β(o)) values were computed by Density Functional Theory and found to be in the range of 67.16 × 10(-31) to 107.76 × 10(-31) e.s.u.

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2,5-Benzodiazocines and intermediates

Cited by 26 publications

References 0 publications

11H-isoindolo[2,1-a]benzimidazoles (Review)

11H-isoindolo[2,1-a]benzimidazoles (Review)

Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity

A Combined Experiment and Computation Study of the Fused Polycyclic Benzimidazole Derivatives

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