Yasemin UNVER, Dilek UNLUER, Sahin DİREKEL, Serdar DURDAGİ

Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies

Since benzo [b ] thiophene scaffold is one of the privileged structures in drug discovery as this core exhibitsactivities for different biological problems, in this study bis (benzo[b ]thiophene-2-yl) alkyl methanimine derivatives (1-9) were synthesized by reacting benzo[b ]thiophene-2-carbaldehyde with diamines. All newly compounds were characterized by IR, 1 H NMR and 13 C NMR spectroscopic methods. Synthesized compounds were investigated using binary QSARbased models on therapeutic activity prediction of synthesized compounds and they showed high predicted activities in following diseases: bacterial, angina, allergy, depression and obesity. Thus, they were then tested for their antimicrobial and antileishmanial activities as a result of this theoretical study. Compound 1(N, N’- (propane-1,3-diyl) bis (1-(benzo [b ] thiophene-2-yl)) methanimine) was found the most active compound in both diseases. Thus, its molecular docking studies were also carried out.

Keywords:

Benzo [b ] thiophene Schiff base, binary QSAR models, molecular docking, antimicrobial and antileishmanial activities,

PDF

___

Banks JL, 2005, J COMPUT CHEM, V26, P1752, DOI 10.1002/jcc.20292
Bas DC, 2008, PROTEINS, V73, P765, DOI 10.1002/prot.22102
Berrade L, 2011, J MED CHEM, V54, P3086, DOI 10.1021/jm2000773
Bryant HU, 1998, P SOC EXP BIOL MED, V217, P45
da Silva CM, 2011, J ADV RES, V2, P1, DOI 10.1016/j.jare.2010.05.004
Daver M, 2002, TETRAHEDRON, V58, P5357 .
Friesner RA, 2006, J MED CHEM, V49, P6177, DOI 10.1021/jm051256o
Jagtap V. A., 2015, J PHARM RES, V9, P10
Jiang JJ, 2003, CHEM PHARM BULL, V51, P1307, DOI 10.1248/cpb.51.1307
Jiang Q, 2019, BIOMED RES INT, V2019, DOI 10.1155/2019/2015978
Keri RS, 2017, EUR J MED CHEM, V138, P1002, DOI 10.1016/j.ejmech.2017.07.038
Khurshid IM, 2008, J ENZYM INHIB, V23, P829, DOI [10.1080/14756360701626082, DOI 10.1080/14756360701626082]
Li H, 2005, PROTEINS, V61, P704, DOI 10.1002/prot.20660
Lianqi JL, 2010, WO Patent, Patent No. [2010/000198, 2010000198, 2010/000198 A1]
Maina ENM, 2020, J COMPLEMENTARY ALTE, V9, P29, DOI [10.9734/jocamr/2020/v9i130134, DOI 10.9734/JOCAMR/2020/V9I130134]
OGETO TK, 2013, ADV LIFE SCI TECH, V13, P9
Ozbilgin A, 2017, ACTA TROP, V173, P90, DOI 10.1016/j.actatropica.2017.05.032
Pettit GR, 2000, ANTI-CANCER DRUG DES, V15, P397
Pettit GR, 2000, ANTI-CANCER DRUG DES, V15, P203
Rao G. K., 2015, CHEM SCI J, V6, P92, DOI DOI 10.4172/2150-3494.100092
Ravi K, 2009, EUR J MED CHEM, V44, P4376, DOI [10.1016/j.ejmech.2009.05.026, DOI 10.1016/J.EJMECH.2009.05.026]
Sastry GM, 2013, J COMPUT AID MOL DES, V27, P221, DOI 10.1007/s10822-013-9644-8
Sener S, 2017, KONURALP TIP DERG, V9, P274, DOI 10.18521/ktd.288157
Shelley JC, 2007, J COMPUT AID MOL DES, V21, P681, DOI 10.1007/s10822-007-9133-z
Unver Y, 2018, LETT DRUG DES DISCOV, V15, P706, DOI 10.2174/1570180814666171012163651
Unver Y, 2016, J ENZYM INHIB MED CH, V31, P89, DOI 10.1080/14756366.2016.1206088
Unver Y, 2014, EUR J MED CHEM, V84, P639, DOI 10.1016/j.ejmech.2014.01.014
Vyas KM, 2011, J MOL STRUCT, V990, P110, DOI 10.1016/j.molstruc.2011.01.024
Yadav P. S., 2011, International Journal of Pharmaceutical Sciences and Drug Research, V3, P1
Yang YP, 2014, EUR J MED CHEM, V87, P703, DOI 10.1016/j.ejmech.2014.10.012