InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives

Lakshmi, Neelakandan Vidhya; Prakasam, Thirumurugan; Noorulla, K. M.; Perumal, Paramasivan T.

doi:10.1016/j.bmcl.2010.07.039

Cited by 63 publications

(23 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…As shown in Scheme 12, compound 33e (R = 2-Cl) was found to exhibit the more potent in vitro antibacterial activity, with MIC values of 12.4, 16.4, 16.5, and 16.1 µM against S. aureus, B. cereus, E. coli, and K. pneumoniae, respectively. In addition, compounds 33a (R = H), 33d (R = 4-Cl), 33h (R = 4-F), and 33m (R = 4-OMe) exhibited significant antibacterial activity when compared to the standard drug ciprofloxacin [54]. A new class of pyrano[3,2-c]chromene derivatives 34 incorporating a validated molecular target was synthesized through a one-pot multicomponent cyclocondensation reaction between β-aryloxyquinoline-3-carbaldehydes 1, 4-hydroxycoumarins 10b and malononitrile (12) in ethanol containing a catalytic amount of piperidine, Scheme 13.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…Different areas converge on the need to synthesize antioxidant compounds as protection against these diseases. Thereby, Lakshmi et al, reported the three-component synthesis of the 3-pyranyl indoles 33 described previously in Scheme 12 [54]. The antioxidant activity of such compounds was determined using methods for antioxidant activity estimation such as DPPH and ABTS.…”

Section: Antioxidant Activitymentioning

confidence: 99%

“…The procedure was accomplished by a tandem Knoevenagel-Michael reaction of 3-cyanoacetyl indole type 32 (X = CN), various aromatic aldehydes 1 and malononitrile (12) catalyzed by InCl 3 in ethanol under refluxing conditions (Scheme 69). The synthesized compounds 33 were evaluated for anticancer activity, in addition to anti-microbial and antioxidant activity, some of them showing good anticancer activity against MCF-7 breast cancer cell lines in comparison with the standard drug used[54]. One-pot three-component methods for the synthesis of 3-pyranylindoles 33 and 4-aryl-6-indolyl-nicotinonitrile-2-ones 144, mediated by 3-acetylindole type 32 as common precursor, for evaluation of their anticancer activity.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

View full text Add to dashboard Cite

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].

show abstract

Section: Antimicrobial Activitymentioning

confidence: 99%

Section: Antioxidant Activitymentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Indole, the potent basic pharmacodynamic nucleus, has been reported to possess a wide variety of biological properties viz., anti-inflammatory, [1][2][3] anticonvulsant, [4] cardiovascular, [5] antitubercular, [6] antioxidant, [7] antiviral, [8] antimalarial [9] and Downloaded by [New York University] at 19: 12 26 May 2015 antimicrobial. [10,11] In particular, 3-substituted indole is the one of the "privileged medicinal scaffold" found in many natural products [12,13] and biologically active compounds especially with anticancer, antitumor, [14] hypoglycemic, anti-inflammatory, analgesic and antipyretic activities.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of 3-(2-Haloacyl)indoles

El‐Mekabaty

2015

Synthetic Communications

View full text Add to dashboard Cite

“…On the other hand, indole derivatives have been a topic of substantial research interest in contemporary heterocyclic and medicinal chemistry due to their great significance in the view of their (i) occurrence in nature as a prominent sub-structure of a large number of alkaloids (Tanaka et al, 2006;Frederich et al, 2008) and (ii) wide-ranging biological activities which includes antimicrobial (Al-Qawasmeh et al, 2010;Tiwari et al, 2006;Harnden et al, 1978), antitubercular (Karthikeyan et al, 2009;Guzel et al, 2008), ghrelin receptor (Demange et al, 2007), anticancer (Singh et al, 2009;Shi et al, 2007), antioxidant (Lakshmi et al, 2010), antiviral (Giampieri et al, 2009;Fonseca et al, 2004), and antimalarial (Kgokong et al, 2005;Agarwal et al, 2005). Literature survey manifests that the number of 4H-chromene derivatives have been synthesized using various aldehydes Patel, 2009a, 2011b;Mungra et al, 2011b) but there is not a single report where 2-phenyl-1H-indole-3-carbaldehyde is used.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of 3′-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

Kathrotiya

Patel

2011

Med Chem Res

View full text Add to dashboard Cite

A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3-carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study.

show abstract

InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives

Cited by 63 publications

References 53 publications

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Chemistry of 3-(2-Haloacyl)indoles

Microwave-assisted synthesis of 3′-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

Contact Info

Product

Resources

About