Enantioselective approach towards the synthesis of spiro-indeno [1,2-b] quinoxaline pyrrolothiazoles as antioxidant and antiproliferative

Mani, Kailasam Saravana; Murugesapandian, Balasubramanian; Kaminsky, Werner; Rajendran, S. P.

doi:10.1016/j.tetlet.2018.06.035

Cited by 31 publications

(5 citation statements)

References 51 publications

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“…3.1.19 | 2-methyl-4H- [1,3]oxazino[4 0 ,5 0 :4,5] selenolo [2,3-b]quinoxalin-4-one (10) Acetic anhydride (10 mL) was used to heat the sodium salt (9) under reflux for 2 h, after which it was cooled. Get brown crystals, m.p.…”

Section: Chemistrymentioning

confidence: 99%

“…Functional modification of quinoxaline can lead to the formation of various valuable compounds that find applications in medicine, agriculture, and the chemical industry. Quinoxaline derivatives have exhibited multiple biological activities such as anticancer activity [1,2], antioxidant activity [3], antiproliferative activity [3,4], antituberculosis activity [5], antibacterial activity [6], and anti-hepatitis C virus activity [7]. They have also shown promising results in the treatment of AIDS [8], depression [9], and glaucoma [10].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Abdelwadoud,

Gomaa,

Geies

2023

Journal of Heterocyclic Chem

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In this paper, we present the synthesis of new selenoloquinoxaline derivatives starting from 2‐chloroquinoxaline‐3‐carbonitrile 1. The compound 1 was subjected to a reaction with selenium metal in the presence of NaBH4 as a reducing agent in ethanol, under a nitrogen atmosphere. This reaction resulted in the formation of the sodium salt of 3‐cyanoquinoxaline‐2‐selenolate, which was subsequently reacted with α‐halogenated carbonyl compounds in situ. This reaction produced a series of newly synthesized 3‐aminoselenolo[2,3‐b]quinoxaline‐2‐substituents. Ethyl 3‐aminoselenolo[2,3‐b]quinoxaline‐2‐carboxylate 3a was hydrolyzed by sodium hydroxide to give the corresponding sodium salt 9. This salt was then refluxed with acetic anhydride to produce oxazinone compound 10. The reaction of compound 10 with ammonium acetate afforded pyrimidoselenolo[2,3‐b]quinoxaline derivative 11. Compound 11 was then chlorinated using phosphorous oxychloride to give the corresponding chlorocompound.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Abdelwadoud,

Gomaa,

Geies

2023

Journal of Heterocyclic Chem

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“…Due to its importance, the synthesis of the quinoline scaffold has been studied for well over a century through the classical methods including the well-known Skraup, Doebner-Miller, Friedländer and Combes reactions, among others [92,93]. In 2006 Kouznetzov et al, reported the three-component cyclization of pyridinecarbaldehydes 1, anilines 2 and indene (100) in the presence of BF 3 ·OEt 2 as catalyst [94]. The process involved an imino Diels-Alder cycloaddition affording the corresponding indeno[2,1-c]quinolines 101 in 32−98% yield (Scheme 42).…”

Section: Quinoline Derivativesmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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“…1). In continuation of research in spiro heterocycles [21][22][23] and the biological signi cance of the above systems, herein we wish to report the synthesis of 3'-benzyl-5'-phenyl-3',3a'-dihydro-2'H-spiro[indoline-3,1'-pyrrolo [3,4-c]pyrrole]-2,4',6' (5'H,6a'H)trione through stereoselective 1,3-dipolar cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

Discovery, synthesis and in silico approach of pyrrolo [3,4- c ]pyrroles as SARS-CoV-2 m ^pro inhibitors

Mani

Rajamanikandan

Prabha

2023

Journal of Biomolecular Structure and Dynamics

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A new series of pyrrolo [3,2-c] pyrroles were synthesized and characterized using various analytical techniques including FT-IR, UV-Vis and NMR spectroscopic studies. The biological descriptors of the synthesized compounds were investigated using DFT calculation. The mode of binding and reactivity of the target compounds with SARS-CoV-2 main protease (M pro ) were studied using molecular docking and molecular dynamics (MD) simulation. Molecular docking of the compounds (4a and 5a) showed a promising binding a nity towards M pro protein with the binding energy of -8.3 kcal/mol and − 8.0 kcal/mol, respectively. The results of MD simulation and prime MM-GBSA calculation were consistent with molecular docking. The absorption, distribution, metabolism, excretion (ADME) properties of the compounds are in the acceptable range, as they are orally active and obey Lipinski's rule of ve without violation. In addition, in silico toxicity prediction using the Pro-Tox II revealed the non-toxic nature of the compounds. Hence the obtained results suggest that these compounds could be a possible anti-viral candidate and highlight this series of compounds for further drug design and development against SARS-CoV-2.

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Enantioselective approach towards the synthesis of spiro-indeno [1,2-b] quinoxaline pyrrolothiazoles as antioxidant and antiproliferative

Cited by 31 publications

References 51 publications

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Discovery, synthesis and in silico approach of pyrrolo [3,4- c ]pyrroles as SARS-CoV-2 m ^pro inhibitors

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Enantioselective approach towards the synthesis of spiro-indeno [1,2-b] quinoxaline pyrrolothiazoles as antioxidant and antiproliferative

Cited by 31 publications

References 51 publications

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Discovery, synthesis and in silico approach of pyrrolo [3,4- c ]pyrroles as SARS-CoV-2 m pro inhibitors

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Discovery, synthesis and in silico approach of pyrrolo [3,4- c ]pyrroles as SARS-CoV-2 m ^pro inhibitors