Imidazole–Thiazole Hybrid: Synthesis, Brain Penetration, Cytochrome P450 Enzyme and Gastrointestinal Absorption Study

Asmaa S (2016) Synthesis, spectral properties and anti-tumor evaluations of some novel 2-substituted-1, 3-thiazole derivatives. Am Chem Sci J 15(3):1–13

Barradas J, Errea M, D’Accorso N, Sepúlveda C, Damonte E (2011) Imidazo [2,1-b] thiazole carbohydrate derivatives: synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever. Eur J Med Chem 46(1):259–264

Brenk R, Schipani A, James D, Krasowski A, Gilbert I, Frearson J (2008) Lessons learnt from assembling screening libraries for drug discovery for neglected diseases. Chem Med Chem 3:435–444

Daina A, Zoete V (2016) BOILED-egg to predict gastrointestinal absorption and brain penetration of small molecules. Chem Med Chem 11(11):1117–1121

Daina A, Michielin O, Zoete V (2014) iLOGP: a simple, robust, and efficient description of n-octanol/water partition coefficient for drug design using the GB/SA approach. J Chem Inf Model 54(12):3284–3301

Daina A, Michielin O, Zoete V (2017) SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep 7:42717

Degreef H, Heeres J, Borgers M (2006) Antifungal azoles for skin disorders. Expert Opin Ther Pat 16(9):1235–1253

Delaney J (2004) ESOL: estimating aqueous solubility directly from molecular structure. J Chem Inf Comput Sci 44(3):1000–1005

Egan W, Merz K, Baldwin J (2000) Prediction of drug absorption using multivariate statistics. J Med Chem 43(21):3867–3877

Fagerberg J, Karlsson E, Ulander J, Hanisch G, Bergstrom C (2015) Computational prediction of drug solubility in fasted simulated and aspirated human intestinal fluid. Pharm Res 32(2):578–589

Gaidhane M, Ghatole A, Lanjewar K, Hatzade K (2020) Innovational combination of hetero-bifunctional N-PEG quinoline scaffolds derivatives with improved anticancer activity against breast and colon cancer cell lines and P-glycoprotein, cytochrome p450 enzyme activity prediction. Turk J Chem 44(6):1495–1514

Ganesh S, Brindha D, Shalini S, Nikhila M, Perumal Y, Dharmarajan S (2016) Design, synthesis and biological evaluation of imidazo [2,1-b] thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitor. Bioorganic Med Chem 24(6):1298–1307

Gatfaoui S, Issaoui N, Mezni A, Bardak F, Roisnel T, Atac A, Marouani H (2017) Synthesis, structural and spectroscopic features, and investigation of bioactive nature of a novel organic-inorganic hybrid material 1H-1, 2, 4-triazole-4-ium trioxonitrate. J Mol Struct 1150:242–257

Geronikaki A, Hadjipavlou-Litina D, Zablotskaya A, Segal I (2007) Organosilicon-containing thiazole derivatives as potential lipoxygenase inhibitors and anti-inflammatory agents. Bioinorg Chem Appl. https://doi.org/10.1155/2007/92145

Ghalla H, Issaoui N, Bardak F, Atac A (2018) Intermolecular interactions and molecular docking investigations on 4-methoxybenzaldehyde. Comput Mater Sci 149:291–300

Ghatole A, Lanjewar K, Gaidhane M (2012) Syntheses, characterization, antimicrobial activity of copper (II), zinc (II) and cobalt (II) complexes of the bi-dented substituted 2-((E)-2-((2-chloro-6-ethoxyquinolin-3-yl)methyleneamino)thiazol-4-yl)phenol havong ON donor site. J Pharm Res 5(5):2758–2762

Ghatole A, Gaidhane M, Lanjewar K, Hatzade K (2020) Pharmacokinetics, drug-likeness, medicinal properties, molecular docking analysis of substituted β-lactams synthesized via [bmim][PF6]/[Et3NH]+[HSO4]- catalyzed coupling reaction. Chem Bulg J Sci Educ 29(2):206–244

Ghose A, Viswanadhan VWJ (1998) Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods. J Phys Chem A 102(21):3762–3772

Ghose A, Viswanadhan V, Wendoloski J (1999) A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem 1(1):55–68

Hann M, Keseru G (2012) Finding the sweet spot: the role of nature and nurture in medicinal chemistry. Nat Rev Drug Discov 11:355–365

Hatzade K, Sheikh J, Taile V, Ghatole A, Ingle V, Genc M, Hadda T (2015) Antimicrobial/antioxidant activity and POM analyses of novel 7-O- -D-Glucopyranosyloxy-3-(4, 5-disubstituted imidazol-2-yl)-4H-chromen-4-ones. Med Chem Res 24:2679–2693

Hatzade K, Ghatole A, Gaidhane P, Gaidhane M, Gadekar G (2021) A facile synthesis of some new pyrimidine-2,4,6-triones analogs and their O-β-D-glucosides P-glycoprotein and antioxidant, antimicrobial study, blood–brain barrier, cytochrome p450 enzyme activity prediction. Med Chem Res 30:163–181

Hu Y, Shen Y, Wu X, Tu X, Wang G (2017) Synthesis and biological evaluation of coumarin derivatives containing imidazole skeleton as potential antibacterial agents. Eur J Med Chem 143:958–969

Issaoui NGH, Brandán S, Bardak F, Flakus H, Atac A, Oujia B (2017a) Experimental FTIR and FT-Raman and theoretical studies on the molecular structures of monomer and dimer of 3-thiopheneacrylic acid. J Mol Struct 135:209–221

Issaoui N, Ghalla H, Bardak F, Karabacak M, Dlala N, Flakus H, Oujia B (2017b) Combined experimental and theoretical studies on the molecular structures, spectroscopy, and inhibitor activity of 3-(2-thienyl) acrylic acid through AIM, NBO, FT-IR, FT-Raman, UV and HOMO-LUMO analyses, and molecular docking. J Mol Struct 1130:659–668

Karim M, Michael S, Kristin W, Beverly S, Daniel G (2004) Effects of the IMP-dehydrogenase inhibitor, Tiazofurin, in bcr-abl positive acute myelogenous leukemia: part I. In vivo studies. Leuk Res 28(11):1125–1136

Lambert C, Wilhelm M, Striebel H, Kradolfer F, Schmidt P (1964) Eine neue gegen Bilharziose und Amoebiase wirksame Verbindung. Kurze Mitteilungen 20:452–453

Lipinski C, Lombardo F, Dominy B, Feeney P (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46(1–3):3–26

Matlock M, Hughes T, Dahlin J, Swamidass S (2018) Modeling small molecule reactivity identifies promiscuous bioactive compounds. J Chem Inf Model 26(5):1483–1500

Mehdi D, Hadi B, Javad B, Nasser L (2008) Theoretical 14N nuclear quadrupole resonance parameters for sulfa drugs: sulfamerazine and sulfathiazole. J Mol Graph Model 27(3):326–331

Muegge I, Heald S, Brittelli D (2001) Simple selection criteria for drug-like chemical matter. J Med Chem 44(12):1841–1846

Sagaama A, Issaoui N (2020) Design, molecular docking analysis of an anti-inflammatory drug, computational analysis and intermolecular interactions energy studies of 1-benzothiophene-2-carboxylic acid. Comput Biol Chem 88:107348

Satbhaiya S, Chourasia O (2015) Syntheses, characterization and antimicrobial activities of 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-(((3aR,5R)-3-5-disubstituted-3,3a-dihydro-2H-pyrazolo[3,4-d]thiazol-6(5H)-yl)amino)ethanone derivatives. Chem Sci Trans 4(3):819–827

Shad H, Hussain A, Shahzad K, Alam M, Ilyas M, Hussain G, Ahmad K (2018) Multi-component synthesis of novel diazoles: their characterization and biological evaluation. Arch Org Inorg Chem Sci 1(2):52–56

Taile V, Hatzade K, Ingle V (2011) Synthesis of 2-(sulfamoylphenyl)-4’-(iminoaryl/hetroaryl)-4-(4’’-hydroxyphenyl)-thiazoles and their O-glucosides. J Heterocycl Chem 48:1428–1433

Teague S, Davis A, Leeson P, Oprea T (1999) The Design of leadlike combinatorial libraries. Angew Chem Int Ed Engl 38(24):3743–3748

Trabelsi S, Issaoui N, Brandán SA, Bardak F, Roisnel T, Atac A, Marouani H (2019) Synthesis and physic-chemical properties of a novel chromate compound with potential biological applications, bis (2-phenylethylammonium) chromate (VI). J Mol Struct 1185:168–182

Tratrat C, Haroun M, Paparisva A, Geronikaki A, Kamoutsis C, C´iric´ A, Saxena A (2018) Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones. Pharmacophore models for antifungal activity. Arabian J Chem 11(4):573–590

Upadhyay S, Zala R, Bhatt K (2020) Synthesis, characterization and biological screening of schiff bases derived from 4, 6-difluoro-2-amino benzothiazole. Med Anal Chem Int J 4(1):1–7

Veber D, Johnson S, Cheng H, Smith B, Ward KK (2002) Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 45(12):2615–2623

Zhu Z, Lu Z, Xu T, Chen C, Yang G, Zha T, Xue Y (2020) Arbidol monotherapy is superior to lopinavir/ritonavir in treating COVID-19. J Infect 81(1):e21–e23