Recent major developments in the synthesis (including solid phase methodologies), chemistry and applications of the fully unsaturated 1,2,4-oxadiazole nucleus are reviewed. The review covers the years 1995–2000.
BoyerJ.H., in Heterocyclic Compounds, ed ElderfieldR.C., Wiley, New York, 1962. Vol. 7, p. 462.
2.
BehrL.C., in The Chemistry of Heterocyclic Compounds, ed WeissbergerA., Wiley, New York, 1962. Vol. 17, p. 245.
3.
EloyF., Fortschr. Chem. Forsch, 1965, 4, 807.
4.
ClappL.B., in Advances in Heterocyclic Chemistry, eds KatritzkyA.R., and BoultonA. J., Academic Press, New York, 1976. Vol. 20, p. 65.
5.
ClappL.B., in Comprehensive Heterocyclic Chemistry, 1st edition, eds ReesC.W., and KatritzkyA. R., Pergamon, Oxford, 1984. Vol. 6, p. 365.
6.
KraatzU., in Methoden Org. Chem. (Houben-Weyl), ed SchaumannE., Thieme, Stuttgart, 1994. Vol. E8c, p. 409.
7.
JochimsJ.C., in Comprehensive Heterocyclic Chemistry, 2nd edition, eds ReesC.W., KatritzkyA. R., and ScrivenE. F. V., Pergamon, Oxford, 1996. Vol. 4, p. 179.
8.
ZhangM.L., CuiY. X., MaL. T., ZhangL. H., LuY., ZhaoB., and ZhengQ. T., Chinese Chem. Lett., 1999, 10, 117.
BatistaH., CarpenterG. B., and SrivastavaR. M., J. Chem. Crystallography, 2000, 30, 131.
11.
Barbieux-FlammangM., VandevoordeS., FlammangR., WongM. H., BibasH., KennardC. H. L., and WentrupC., J. Chem. Soc., Perkin Trans. 2, 2000, 473.
12.
WitanowskiM., BiedrzyckaZ., SicinskaW., GrabowskiZ., and WebbG. A., J. Magn. Reson. (A), 1996, 120, 148.
13.
LeiteL.F. C. C., BarreiroE. J., RamosM. N., SilvaJ. B. P., GaldinoS. L., and PittaI. R., Spectroscopy, 2000, 14, 115.
14.
NobeliI., PriceS. L., LommerseJ. P. M., and TaylorR., J. Comput. Chem., 1997, 18, 2060.
15.
MinkinV.I., GarnovskiiA. D., ElgueroJ., KatritzkyA. R., and DeniskoO. V., in Advances in Heterocyclic Chemistry, eds KatritzkyA.R., and BoultonA. J., Academic Press, New York, 2000, p. 157.
16.
(a) LiangG.-B., and FengD. D., Tetrahedron Letters, 1996, 37, 6627.
17.
AntunesR., BatistaH., SrivastavaR. M., ThomasG., and AraujoC. C., Bioorg. Med. Chem. Lett., 1998, 8, 3071.
18.
HébertN., HannahA. L., and SuttonS. C., Tetrahedron Lett., 1999, 40, 8547 and references therein.
19.
DeeganT.L., NitzT. J., CebzanovD., PufkoD. E., and PorcoJ. A., Bioorg. Med. Chem. Lett., 1999, 9, 209.
20.
FengD.D., BiftuT., CandeloreM. R., CascieriM. A., ColwellL. F., DengL., FeeneyW. P., ForrestM. J., and HomG. J., MacIntyreD. E., MillerR. R., StearnsR. A., StraderC. D., TotaL., WyvrattM. J., FisherM. H., and WeberA. E., Bioorg. Med. Chem. Lett., 2000, 10, 1427.
21.
BiftuT., FengD. D., LiangG.-B., KuoH., QianX., NaylorE. M., ColandreaV. J., CandeloreM. R., CascieriM. A., ColwellL. F., ForrestM. J., HomG. J., MacIntyreD. E., StearnsR. A., StraderC. D., WyvrattM. J., FisherM. H., and WeberA. E., Bioorg. Med. Chem. Lett., 2000, 10, 1431.
(a) BuchananJ.L., VuC. B., MerryT. J., CorpuzE. G., PradeepanS. G., ManiU. N., YangM., PlakeH. R., VarkhedkarV. M., LynchB. A., MacNeilI. A., LoiaconoK. A., TiongC. L., and HoltD. A., Bioorg. Med. Chem. Lett., 1999, 9, 2359.
24.
VuC.B., CorpuzE. G., MerryT. J., PradeepanS. G., BartlettC., BohacekR. S., BotfieldM. C., EyermannC. J., LynchB. A., MacNeilI. A., RamM. K., van SchravendijkM. R., VioletteS., and SawyerT. K., J. Med. Chem., 1999, 42, 4088.
25.
BorgS., VollingaR. C., LabarreM., PayzaK., TereniusL., and LuthmanK., J. Med. Chem., 1999, 42, 4331.
26.
(a) MenzlerS., BikkerJ. A., and HorwellD. C., Tetrahedron Lett., 1998, 39, 7619.
GangloffA.R., LitvakJ., SheltonE. J., SperandioD., WangV. R., and RiceK. D., Tetrahedron Lett., 2001, 42, 1441.
32.
(a) VieiraR.F., BrondaniD. J., de FariaA. R., SrivastavaR. M., and LeiteA. C. L., Heterocycl. Commun., 1999, 5, 521.
33.
SrivastavaR.M., da Canceicao PereiraM., HallwassF., and PachecoC. R. N., Heterocycles, 1999, 51, 2961.
34.
SrivastavaR.M., de Assunção Borges VianaM. B., and BieberL., J. Heterocycl. Chem., 1984, 21, 1193.
35.
(a) LeiteL.F. C. C., RamosM. N., da SilvaJ. B. P., MirandaA. L. P., FragaC. A. M., and BarreiroE. J., Il Farmaco, 1999, 54, 747.
36.
DianaG.D., VolkotsD. L., NitzT. J., BaileyT. R., LongM. A., VescioN., AldousS., PevearD. C., and DutkoF. J., J. Med. Chem., 1994, 37, 2421.
37.
KajukovaL.A., PralievK. D., ZhumadildajevaI. S., and KrepikovaS. G., Khim. Getetrosikl. Soedin, 1999, 701.
38.
RiceK.D., and NussJ. M., Bioorg. Chem. Med. Lett., 2001, 11, 753.
39.
SamsC.K., and LauJ., Tetrahedron Lett., 1999, 40, 9359.
40.
(a) ZhangH., El-AssadiA. A., EdgarM. A. N., and MesserW. S., Abstracts of Presentations, 211th National Meeting of the ACS, March 24, 1996; Volume 211, Division of Medicinal Chemistry, Abstract 033-MEDI.
41.
ClitherowJ.W., BeswickP., IrvingW. J., ScopesD. I. C., BarnesJ. C., ClaphamJ., BrownJ. D., EvansD. J., and HayesA. G., Bioorg. Med. Chem. Lett., 1996, 6, 833.
42.
MacorJ.E., OrdwayT., SmithR. L., VerhoestP. R., and MackR. A., J. Org. Chem., 1996, 61, 3228.
43.
SuzukiT., IwaokaK., ImanishiN., NagakuraY., MiyatiK., NakaharaH., and OhtaM., and MaseT., Chem. Pharm. Bull., 1999, 47, 120.
44.
DolbierW.R., BurkholderC. R., and MédebielleM., J. Fluorine Chem., 1999, 95, 127.
CostanzoA., GuerriniG., CicianiG., BruniF., SelleriS., CostaB., MartiniC., LucacchiniA., AielloP. M., and IpponiA., J. Med. Chem., 1999, 42, 2218.
64.
BencharifL., TallecA., and TardivelR., Electrochimica Acta, 1997, 42, 3509.
65.
(a) TorssellK.G. B., in Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, UCA, Berlin, 1988.
66.
CaramellaP., and GrünangerP., in 1,3-Dipolar Cycloaddition Chemistry, ed. PadwaA., Wiley, New York, 1984. Vol. 1, pp. 291.
67.
GreigD.J., HamiltonD. G., McPhersonM., PatonR. M., and CrosbyJ., J. Chem. Soc., Perkin Trans. 1, 1987, 607.
68.
HumphreyG.R., and WrightS. H. B., J. Heterocycl. Chem., 1989, 26, 23.
69.
TegelerJ.J., and DiamondC. J., J. Heterocycl. Chem., 1987, 24, 697 and 701.
70.
MiddletonW.J., J. Org. Chem., 1984, 49, 919.
71.
LenaersR., and EloyR., Helv. Chim. Acta, 1963, 43, 1067.
72.
Díaz-OritzA., Díez-BarraE., de la HozA., MorenoA., Gómez-EscalonillaM. J., and LoupyA., Heterocycles, 1996, 43, 1021.
73.
BeltrameP., CadoniE., FlorisC., GelliG., and LaiA., Heterocycles, 2000, 53, 1915.
74.
GiurgM., and Ml/ochowskiJ., Polish J. Chem., 1997, 71, 1093.
75.
KijimaM., NakazatoK., and SatoT., Chem. Lett., 1994, 347.
76.
(a) NeidleinR., and LiS., Synth. Commun., 1995, 25, 2379.
77.
NeidleinR., and LiS., J. Heterocycl. Chem., 1996, 33, 1943.
78.
NeidleinR., KramerW., and LiS., J. Heterocycl. Chem., 1998, 35, 161.
79.
NicolaidesD.N., FylaktakidouK. C., LitinasK. E., and Hadjipavlou-LitinaD., J. Heterocycl. Chem., 1996, 33, 967.
80.
QuadrelliP., InvernizziA. G., FalzoniM., and CaramellaP., Tetrahedron, 1997, 53, 1787.
81.
(a) JochimsJ.C., in Comprehensive Heterocyclic Chemistry, 2nd edition, eds ReesC.W., KatritzkyA. R., and ScrivenE. F. V., Pergamon, Oxford, 1996. Vol. 4, pp. 211.
82.
ClappL.B., in Advances in Heterocyclic Chemistry, eds KatritzkyA.R., and BoultonA. J., Academic Press, New York, 1976. Vol. 20, pp. 76.
83.
(a) JohnsonJ.E., NwokoD., HotemaM., SanchezN., AldermanR., and LynchV., J. Heterocycl. Chem., 1996, 33, 1583.
84.
SrivastavaR.M., de MoraisL. P. F., CatanhoM. T. J. A., de SouzaG. M. L., SeabraG. M., SimasA. M., and RodriguesM. A. L., Heterocycl. Commun., 2000, 6, 41.
85.
HemmingK., MorganD. T., and SmalleyR. K., J. Fluorine Chem., 2000, 106, 83.
86.
BuscemiS., FrennaV., VivonaN., PetrilloG., and SpinelliD., Tetrahedron, 1995, 51, 5133.
87.
(a) van der PlasH.C., J. Heterocycl. Chem., 2000, 37, 427.
88.
van der PlasH.C., Advances in Heterocyclic Chemistry, eds KatritzkyA.R., Academic Press, New York, 1999. Vol. 74, pp. 1.
89.
BuscemiS., PaceA., and VivonaN., Tetrahedron Lett., 2000, 41, 7977.
90.
ZhangY.-X., SasakiK., and HirotaT., J. Heterocycl. Chem., 1999, 36, 787.
91.
QuadrelliP., MellaM., and CaramellaP., Tetrahedron Lett., 1999, 40, 797.
92.
BarrettA.G. M., CramoS. M., RobertsR. S., and ZecriF. J., Comb. Chem. High Throughput Screen., 2000, 3, 131.
93.
(a) BaileyN., CooperA. W. J., DealM. J., DeanA. W., GoreA. L., HawesM. C., JuddD. B., MerrittA. T., StorerR., TraversS., and WatsonS. P., Chimia, 1997, 51, 832.
94.
WilliamsJ.P., and LavradorK., Comb. Chem. High Throughput Screen., 2000, 3, 43.
95.
BurkholderC., DolbierW. R., and MédebielleM., J. Org. Chem.1998, 63, 5385.
96.
FrennaV., MacalusoG., ConsiglioG., CosimmelliB., and SpinelliD., Tetrahedron, 1999, 55, 12885.
97.
La MannaG., BuscemiS., and VivonaN., J. Molecular Structure (Theochem), 1998, 452, 67.
98.
(a) BuscemiS., VivonaN., and CaronnaT., J. Org. Chem., 1995, 60, 4096.
99.
BuscemiS., VivonaN., and CaronnaT., J. Org. Chem., 1996, 61, 8397.
100.
VivonaN., BuscemiS., AstaS., and CaronnaT., Tetrahedron, 1997, 53, 12629.
101.
BuscemiS., PaceA., VivonaN., CaronnaT., and GaliaA., Tetrahedron, 1997, 53, 12629.
102.
LiaoY., BöttcherH., HartingJ., GreinerH., van AmsterdamC., CremersT., SundellS., MärzJ., RautenbergW., and WikströmH., J. Med. Chem., 2000, 43, 517.
103.
da SilvaA.S., de SilvaM. A. A., CarvalhoC. E. M., AntunesO. A. C., HerreraJ. O. M., BrinnI. M., and MangrichA. S., Inorg. Chim. Acta, 1999, 292, 1.
104.
(a) JochimsJ.C., in Comprehensive Heterocyclic Chemistry, 2nd edition, eds ReesC.W., KatritzkyA. R., and ScrivenE. F. V., Pergamon, Oxford, 1996. Vol. 4, p. 224.
105.
LuthmanK., BorgS., and HacksellU., Methods Mol. Med., 1999, 23, 1.
106.
FleckensteinA.E., KopajticT. A., BojaJ. W., CarrollF. I., and KuharM. J., Eur. J. Pharmacol., 1996, 311, 109 and references therein.
107.
(a) GasterL.M., BlaneyF. E., DaviesS., DuckworthD. M., HamP., JenkinsS., JenningsA. J., JoinerG. F., KingF. D., MulhollandK. R., WymanP. A., HaganJ. J., HatcherJ., JonesB. J., MiddlemissD. N., PriceG. W., RileyG., RobertsC., RoutledgeC., SelkirkJ., and SladeP. D., J. Med. Chem., 1998, 41, 1218.
108.
SelkirkJ.V., ScottC., HoM., BurtonM. J., WatsonJ., GasterL. M., CollinL., JonesB. J., MiddlemissD. N., and PriceG. W., Br. J. Pharmacol., 1998, 125, 202.
see HeyJ. A., and ShihN. Y., in Annual Reports in Medicinal Chemistry, 2000, 35, 53.
112.
AcriJ.B., WongG., and WitkinJ. M., Eur. J. Pharmacol., 1995, 278, 213 and references therein.
113.
(a) MickelsonJ.W., JacobsenE. J., CarterD. B., ImH. K., ImW. B., SchreurP. J. K. D., SethyV. H., TangA. H., McGeeJ. E., and PetkeJ. D., J. Med. Chem., 1996, 39, 4654.
114.
AtorN.A., and GriffithsR. R., J. Pharmacol. Exp. Ther., 1999, 289, 1434.
115.
WieczorekM., GyorkosA., SpruceL. W., EttingerA., RossS. E., KroonaH. S., Burgos-LepleyC. E., BrattonL. D., DrennanT. S., GarnertD. L., von BurgG., PilkingtonC. G., and CheronisJ. C., Arch. Biochem. Biophys., 1999, 367, 193.
116.
ChimirriA., GrassoS., MontforteA.-M., RaoA., and ZappalaM., Il Farmaco, 1996, 51, 125.
117.
VuC.B., CorpuzE. G., PradeepanS. G., VioletteS., BartlettC., and SawyerT. K., Bioorg. Med. Chem. Lett., 1999, 9, 3009.