Abstract
Several trans- and cis-2-acetyl-3-(substituted-phenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole derivatives have been synthesised via the condensation of the appropriate exocyclic α,β-unsaturated ketones with hydrazine in hot acetic acid, to obtain diastereomeric mixtures of N-acetylated isomers. Structure elucidation was based on their spectral data and the trans–cis stereochemistry using of NOE and NOESY experiments. Biological testing of these derivatives as inhibitors of β-hematin formation was carried out.
References
1.
Thangadurai A.
,
Minu M.
,
Wakode S.
,
Agrawal S.
, and
Narasimhan B.
, Med. Chem. Res. , 2012 , 21 , 1509 .
2.
Collins I.
,
Rowley M.
,
Davey W.
,
Emms F.
,
Marwood R.
,
Patel S.
,
Patel S.
,
Fletcher A.
,
Ragan I.
,
Leeson P.
,
Scott A.
, and
Broten T.
, Bioorg. Med. Chem. , 1998 , 6 , 743 .
3.
Mishriky N.
,
Ibrahim Y.
,
Girgis A.
, and
Fawzy G.
, Pharmazie , 1999 , 54 , 738 .
4.
Murineddu G.
,
Ruiu S.
,
Mussinu J.-M.
,
Loriga G.
,
Grella G.
,
Carai M.
,
Lazzari P.
,
Pani L.
, and
Pinna G.
, Bioorg. Med. Chem. , 2005 , 13 , 3309 .
5.
Lokhande P.
,
Kuchekar B.
,
Chabukswar A.
, and
Jagdale S.
, Asian J. Biochem. , 2006 , 1 , 1 .
6.
Meyers M.
,
Arhancet G.
,
Hockerman S.
,
Chen X.
,
Long S.
,
Mahoney M.
,
Rico J.
,
Garland D.
,
Blinn J.
,
Collins J.
,
Yang S.
,
Huang H.
,
McGee K.
,
Wendling J.
,
Dietz J.
,
Payne M.
,
Homer B.
,
Heron M.
,
Reitz D.
, and
Hu X.
, J. Med. Chem. , 2010 , 53 , 5979 .
7.
Wiley R.
, Chem Heterocycl Compd (NY) , 1967 , 22 , 3 –366 .
8.
Lévai A.
, J. Heterocyclic Chem. , 2002 , 39 , 1 .
9.
Lévai A.
,
Kövér K.
, and
Jekö J.
, ARKIVOC , 2007 , viii , 26 .
10.
Lévai A.
,
Szöllósy Á.
, and
Tóth G.
, J. Chem. Res. (S). , 1985 , 392 .
11.
El-Rayyes N.
, and
Al-Jawhary A.
, J. Heterocyclic Chem. , 1986 , 23 , 135 .
12.
Sangwan N.
, J. Chem. Res. (S). , 1987 , 22 .
13.
Faidallah H.
, and
Makki M.
, J. Chin. Chem. Soc. , 1994 , 41 , 585 .
14.
Lóránd T.
,
Aradi F.
,
Szöllösy Á.
,
Tóth G.
, and
Kónya T.
, Monatsh. Chem. , 1996 , 127 , 971 .
15.
Peesapati V.
,
Sreelakshmi P.
, and
Anuradha K.
, J. Chem. Res. (S). , 2001 , 372 .
16.
Charris J.
,
Domínguez J.
,
Gamboa N.
,
Rodrigues J.
, and
Ángel J.
, Eur. J. Med. Chem. , 2005 , 40 , 875 .
17.
Barazarte A.
,
Camacho J.
,
Domínguez J.
,
Lobo G.
,
Gamboa N.
,
Rodrigues J.
,
Capparelli M.
,
Alvarez-Larena A.
,
Andujar S.
,
Enriz D.
, and
Charris J.
, Bioorg. Med. Chem. , 2008 , 16 , 3661 .
18.
Barazarte A.
,
Lobo G.
,
Gamboa N.
,
Rodrigues J.
,
Capparelli M.
,
Álvarez-Larena Á.
,
López S.
, and
Charris J.
, Eur. J. Med. Chem. , 2009 , 44 , 1303 .
19.
Romero A.
,
Acosta M.
,
Gamboa N.
,
Charris J.
,
Salazar J.
, and
López S.
, Bioorg. Med. Chem. , 2015 , 23 , 4755 .
20.
Breitmaier E.
, and
Voelter W.
, Carbon-13 NMR spectroscopy-high resolution methods and applications in organic chemistry and biochemistry. VCH , Weinhein , 1990 , 3rd edn.
21.CAChe reference, version 6.0. Fujitsu Limited CAChe , 2003 .
22.
Allinger N.
,
Yuh Y.
, and
Lii H.
, J. Am. Chem. Soc. , 1989 , 111 , 8551 .
23.
Lokhande P.
,
Hasanzadeh K.
,
Khaledi H.
, and
Ali H.
, J. Heterocyclic Chem. , 2012 , 49 , 1398 .
24.
Wang F.
,
Zhang R.
,
Cui Y.
,
Sheng L.
,
Sun Y.
,
Tian W.
,
Liu X.
, and
Liang S.
, Res. Chem. Intermed. , 2017 , 43 , 5933 .
25.
Peakr D.
,
Robinsona R.
, and
Walker J.
, J. Chem. Soc. , 1936 , 752 .
26.
Fies M.
, and
Friedrich K.
, J. Prakt. Chem. , 1995 , 337 , 50 .
27.
Gautam Y.
,
Dwivedi S.
,
Srivastava A.
,
Hamidullah H.
,
Singh A.
,
Chanda D.
,
Singh J.
,
Rai S.
,
Konwar R.
, and
Negi A.
, RSC Adv. , 2016 , 6 , 33369 . https://doi.org/10.1039/C6RA02663J.
