Synthesis and biological screening of 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles as antiproliferative and anti-inflammatory agents

Rapolu, Sreevani; Manjula, A.; Bommena, Vittal Rao; Murthy, Ramalinga; Jain, Nishant; Bommareddy, Venkata Ramya; Bommineni, Madhava Reddy

doi:10.1016/j.ejmech.2013.05.024

Cited by 42 publications

(23 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4.3. General procedure for preparation of indole-3-carboxylic acid hydrazides (3a-c): (Rapolu et al, 2013) 4.4. General procedure for the synthesis of 5-substituted 1H-indole-3-carbaldehyde (5a,b): (James and Snyder, 1959;Choppara et al, 2015) To a solution of substituted indoles (4a,b) (42.6 mmol) in dry DMF (187.4 mmol) in an ice-salt bath, POCl3 (47.1 mmol) is subsequently added with stirring over a period of 30 min.…”

Section: General Procedures For Preparation Of Indole-3-carboxylates (mentioning

confidence: 99%

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

Choppara

Bethu

Prasad

et al. 2019

Arabian Journal of Chemistry

View full text Add to dashboard Cite

Two series of novel bis(indole) analogues viz., N 0 -((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a-f) and N 0 -((5-substituted-1-(3-methylbut-2-e nyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a-f) were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial, anticancer activities and structure and activity relationship (SAR) was investigated. Compounds 7a, 7c and 8a were found to be active in antimicrobial screening. Anticancer screening reveals that Compound 7c was active against HeLa cell line with an IC 50 of 43.1 lM and compound 7d was found to be interesting candidate with an IC 50 of 26.0 and 30.2 lM against Colo-205 and Hep G2 cell lines respectively. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

show abstract

Section: General Procedures For Preparation Of Indole-3-carboxylates (mentioning

confidence: 99%

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

Choppara

Bethu

Prasad

et al. 2019

Arabian Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…Rapolu et al, synthesized a series of 5-(alkyl(1H-indol-3yl))-2-(substituted)-1,3,4-oxadiazoles using di (acetoxy) iodobenzene followed by their anti-inflammatory activity using rat paw edema method. Compound 6 exhibited the best anti-inflammatory activity [20].…”

Section: Anti-inflammatory Analgesic Ulcerogenic and Lipid Peroxidatmentioning

confidence: 99%

1, 3, 4-Oxadiazole: A Versatile Therapeutic Heterocycle

Sharma¹

2014

abp

View full text Add to dashboard Cite

1, 3, 4-oxadiazole emerged as an important heterocyclic nucleus for new drug development. These compounds have importance as biological targets. This article describes the various methods of synthesis and different bioactivity profiles of 1,3,4-oxadiazole ring system which have been reported within last five years and is helpful in the invention of newer compounds with antimicrobial, antimycobacterial, anti-tumor, antitubercular, anticonvulsant activities and so forth.

show abstract

“…The most popular method for synthesizing the 1,3,4-oxadiazole scaffold involves cyclization of N,N -diacylhydrazine promoted by SOCl 2 [14], BF 3 •Et 2 O [15], TsCl and various bases including 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), Et 3 N, pyridine [16]. Alternatively, some reports have described (i) oxidative cyclization of N-acylhydrazones with different oxidizing agents, such as Dess-Martin periodinane (DMP) [17], N-chlorosuccinimide (NCS) and DBU [18], (diacetoxyiodo)benzene [19], KMnO 4 [20] or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) [21], (ii) photoisomerization of 1,2,4-oxadiazoles [22], (iii) heterocyclization of semicarbazide, thiosemicarbazide, or selenosemicarbazide derivatives [23,24], or (iv) N-acylation followed by ring opening/closing of tetrazoles [25,26].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Novel 1,3,4-Oxadiazoles Bearing a 4-N,N-Dimethylaminoquinazoline Scaffold via Palladium-Catalyzed Suzuki Cross-Coupling Reactions

Wołek¹,

Werłos²,

Komander³

et al. 2020

Molecules

View full text Add to dashboard Cite

Two series of novel (symmetrical and unsymmetrical) quinazolinylphenyl-1,3,4-oxadiazole derivatives were synthesized using palladium-catalyzed Suzuki cross-coupling reactions. The presented synthetic methodology is based on the use of bromine-substituted 2-phenyl-4-N,N-dimethylaminoquinazolines and either a boronic acid pinacol ester or a diboronic acid bis(pinacol) ester of 2,5-diphenyl-1,3,4-oxadiazole. The reactions are conducted in a two-phase solvent system in the presence of catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), sodium carbonate, and tetrabutylammonium bromide, which plays the role of a phase-transfer catalyst. The luminescence properties of the obtained compounds are discussed in the context of applying these compounds in optoelectronics. Specifically, two highly-conjugated final products: N,N-dimethyl-2-phenyl-6-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)quinazolin-4-amine (8f) and 6,6′-(4,4′-(1,3,4-oxadiazole-2,5-diyl)bis(4,1-phenylene))bis(N,N-dimethylquinazolin-4-amine (9f), which contain a 1,3,4-oxadiazole moiety connected to a quinazoline ring by a 1,4-phenylene linker at the 6 position, exhibit strong fluorescence emission and high quantum yields.

show abstract

Synthesis and biological screening of 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles as antiproliferative and anti-inflammatory agents

Cited by 42 publications

References 29 publications

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

1, 3, 4-Oxadiazole: A Versatile Therapeutic Heterocycle

Efficient Synthesis of Novel 1,3,4-Oxadiazoles Bearing a 4-N,N-Dimethylaminoquinazoline Scaffold via Palladium-Catalyzed Suzuki Cross-Coupling Reactions

Contact Info

Product

Resources

About