A series of 3,3-dimethyl-3Hbenzothieno[3,2-f][1]-benzopyran analogues modified at the pyran 1,2-double bond were synthesized. The corresponding dihydro and (±)-cis-diol derivatives were converted into diacetate and cyclic carbonate upon acylation. The title compounds were characterized by spectroscopic analysis and screened for their antimicrobial activity in vitro.
NicolaouK.C., PfefferkornJ.A., RoeckerA.J., CaoG.Q., BarluengaS., MitchellH.J. (2000) Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans. Journal of the American Chemical Society, 122, 9939–9953.
2.
AdebayoA.H., JigC.J., ZhangY.M., HeW.J., ZengG.Z., HanH.J., XuJ.J., AkindahunsiA.A., TanaN.H. (2011) A new chromene isolated from Ageratum conyzoides. Natural Product Communications, 6, 1263–1265.
3.
HaridyM.A., MohamedA.E.H. (2008) New derivatives of chromene and acetoxyeudesmane obtained by microbial transformation. Natural Product Communications, 3, 799–803.
4.
BenslimaneA.F., PouchusY.F., Le BoterffJ., VerbistJ.F., RoussakisC., MonniotF. (1988) Cytotoxic and antibacterial substances from the ascidian Aplidium antillense. Journal of Natural Products, 51, 582–583.
5.
BandaraB.M.R., HewageC.M., KarunaratneV., WannigamaG.P., AdikaramN.K.B. (1992) An antifungal chromene from Eupatorium riparium. Phytochemistry, 31, 1983–1985.
6.
(a) El-NaggarA.M., AhmedF.M.S., El-SalamA.M., DoniaS.G. (1982) Synthesis and biological activity of some new 1-, 2-, and 8-substituted dibenzothiophene amino acid derivatives. Acta Pharmaceutica Jugoslavica, 32, 257–265. (b) Shafiee A, Vossoghi M, Wossooghi J, Yazdani S. (1981) Synthesis and antibacterial and antifungal activities of alkyl and polyhalophenyl esters of benzo[b]thiophene-3-carbamic acid. Journal of Pharmaceutical Sciences, 70, 566–568.
7.
(a) NakibT.A.I., MeeganM.J., LooneyA.M., BurkeM.L. (1992) Synthesis and antifungal activity of some 2-aryl-3-hydroxymethylbenzo[b]thiophenes. European Journal of Medicinal Chemistry, 27, 971–976;(b) Ferreira ICFR, Calhelha RC, Estevinho LM, Queiroz MRP. (2004) Screening of antimicrobial activity of diarylamines in the 2,3,5- trimethylbenzo[b]thiophene series: a structure-activity evaluation study. Bioorganic Medicinal Chemistry Letters, 14, 5831–5833.
8.
BoulwareS.L., BronsteinJ.C., NordbyE.C., WeberP.C. (2001) Identification and characterization of a benzothiophene inhibitor of herpes simplex virus type 1 replication which acts at the immediate early stage of infection. Antiviral Research, 51, 111–125.
YadavJ.S., Subba ReddyB.V., SrinivasC., SrihariP. (2001) Ultrasound-promoted deoxygenation of sulphoxides by Samarium - NH4Cl. Synlett, 6, 854–856.
11.
(a) National Committee for Clinical Laboratory Standards (2002). Reference method for broth dilution antifungal susceptibility testing of yeasts; Approved Standard M27-A NCCLS, Wayne, PA; (b) Clinical and Laboratory Standards Institute (2006) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved Standard M7-A5 CLSI. Wayne, PA.
