A new class of spiroheterocycles-pyrazolinyl thienofuranones and isoxazolinyl thienofuranones were prepared from benzylidene thienofuranones by 1,3-dipolar cycloaddition of nitrile imines and nitrile oxides. The dipolar reagents were generated from araldehyde phenylhydrazones and araldoximes in the presence of phase transfer catalyst. All the compounds are tested for their antimicrobial activity. Chloro substituted pyrazolinyl and isoxazolinyl thienofuranones displayed prominent antibacterial activity against B. subtilis greater than the standard drug Chloramphenicol and antifungal activity against A. niger greater than Ketoconazole.
REFERENCES
1.
Y.
Issa
, N.
Manijeh
, S.
Esmat
, Monatsh Chem.
146
, 2135
–2138
(2015
).2.
A.A.
Salim
, Z.G.
Khalil
, R.J.
Capon
, Tetrahedron.
68
, 9802
–9807
(2012
).3.
A.
Bishnoi
, S.
Singh
, K.A.
Tiwari
, S.
Krishna
, R.
Raghuvir
, M.T.
Chandrakant
, J. Chem. Sci.
125
, 305
–310
(2013
).4.
R.R.
Kumar
, S.
Perumal
, S.C.
Manju
, P.
Bhatt
, P.
Yogeeswari
, D.
Sriram
, Bioorg. Med. Chem. Lett.
19
, 3461
–3465
(2009
).5.
N.
Najim
, Y.
Bathich
, M.M.
Zain
, A.H.
Hamzah
, Z.
Shaameri
, Molecules.
15
(12
), 9340
–9353
(2010
).6.
P.
Das
, A.O.
Omollo
, L.J.
Sitole
, E.
McClendon
, E.J.
Valente
, D.
Raucher
, L.R.
Walker
, A.T.
Hamme
, Tetrahedron.
68
, 9802
–9808
(2012
).7.
A.
Monteiro
, L.M.
Goncalves
, M.M.M.
Santos
, Eur. J. Med. Chem.
79
, 266
–272
(2014
).8.
W.L.
Chan
, M.
Ding
and B.
Zou
, PCT Int. Appl
, WO 2014167528 A1 20141016, (2014
).9.
M.
Kamata
and T.
Yamashita
, Jpn. Kokai Tokkyo Koho
, JP 2009196966 A 20090903, (2009
).10.
V.
Padmavathi
, B.J.M.
Reddy
, A.
Baliah
, A.
Padmaja
, D.B.
Reddy
, Arkivoc.
14
, 1
–13
(2005
).11.
K.
Sudheer
, B.C.
Venkatesh
, K.
Syamaiah
, V.
Padmavathi
, Indian J. Chem.
52B
, 1473
–1478
(2013
).12.
V.
Padmavathi
, K.
Sudheer
, A.
Muralikrishna
, A.
Padmaja
. Indian J. Chem.
54B
, 283
–289
(2015
).13.
Z.
Cheng
, D.
Shanliang
, Z.
Yang
, H.
Ciwang
, C.
Jiaolong
, Z.
Jingsen
, Q.
Lihua
, X.
Xinfang
, Org. Biomol. Chem.
16
, 688
–692
(2018
).14.
G.
Subramaniyan
, R.
Raghunathan
, A.M.M.
Castro
, Tetrahedron.
59
, 335
–340
(2003
).15.
J.
Jayashankaran
, R.D.R.S.
Manian
, R.
Raghunathan
, Tetrahedron Lett.
45
, 7303
–7305
(2004
).16.
D.
Sureshbabu
, E.J.
Valente
, A.T.
Hamme
, Tetrahedron Lett.
55
, 2208
–2211
(2014
).17.
V.
Padmavathi
, T.
Radhalakshmi
, K.
Mahesh
, A.
Padmaja
, Chem. Pharm. Bull.
57
, 1200
–1205
(2009
).18.
G.
Mallikarjuna Reddy
, P.
Ramachandra Reddy
, V.
Padmavathi
, A.
Padmaja
, Arch. Pharm. Chem.Life Sci.
346
, 154
–162
(2013
).19.
T.
Sreelatha
, D.
Seenaiah
, C.
Prema Kumari
, A.
Padmaja
, V.
Padmavathi
, J. Heterocyclic Chem.
52
, 756
–762
(2015
).20.
D.V.
Sowmya
, G.L.
Teja
, A.
Padmaja
, V.K.
Prasad
, V.
Padmavathi
, Eur. J. Med. Chem.
143
, 891
–898
(2018
).
This content is only available via PDF.
© 2019 Author(s).
2019
Author(s)
You do not currently have access to this content.