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Research Article

Synthesis and biological evaluation of some novel tetrahydroquinolines as anticancer and antimicrobial agents

Hassan M. FaidallahDepartment of Chemistry, Faculty of Science, King Abdulaziz University JeddahSaudi ArabiaCorrespondence[email protected]

Alaa A. SaqerDepartment of Chemistry, Faculty of Science, King Abdulaziz University JeddahSaudi Arabia

Khalid A. AlamryDepartment of Chemistry, Faculty of Science, King Abdulaziz University JeddahSaudi Arabia

Khalid A. KhanDepartment of Chemistry, Faculty of Science, King Abdulaziz University JeddahSaudi Arabia

Abdullah M. AsiriDepartment of Chemistry, Faculty of Science, King Abdulaziz University JeddahSaudi Arabia;Center of Excellence for Advanced Materials Research, King Abdulaziz University JeddahSaudi Arabia

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Table 4. Cytotoxic effects (LC₅₀; μM)^a of the active compounds on some human tumor cell lines using the MTT assay.

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Table 5. Minimal inhibitory concentrations [MIC, µg/mL (μM)] of the tested compounds.

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Scheme 1. Reagents and reaction conditions: (i) 2-methylcyclohexanone (0.01 mol), approp. aldehyde (0.01 mol) malononitrile (0.01 mol), NH₄OAc (0.08 mol) in Abs. EtOH (50 mL), reflux 3–6 h; (ii) approp. starting compd. (0.01 mol), formic acid (5 mL), heated in boiling water bath 30 min; (iii) approp. starting compd. (0.01 mol), Ac₂O (5 mL), conc. H₂SO₄ (0.5 mL), heated in boiling water bath 10 min; (iv) approp. starting compd. (0.01 mol), PhNCS (0.01 mol) in pyridine (15 mL), reflux 2 h; (v) approp. starting compd. (0.02 mol), PhCONCS (0.02 mol), dry acetone (10 mL), reflux 3 h; (vi) approp. thioureido deriv. (0.02 mol), 1N NaOH (5.5 mL), EtOH (10 mL), heated in boiling water bath 30 min; (vii) approp. starting compd. (0.001 mol), urea or thiourea (0.005 mol), fused at 260–300 °C, sand bath 1 h; (viii) approp. starting compd. (0.001 mol), urea or thiourea (0.005 mol), heated in microwave reactor at 250 °C, 15 min; (ix) approp. thione (0.02 mol), 1N NaOH (5 mL), EtOH (2 mL), alkyl or aralkyl halide (0.022 mol), stirred at r.t., 2–3 h and (x) approp. starting compd. (0.01 mol), HCONH₂ (10 mL), reflux, 2–3 h.

Scheme 1. Reagents and reaction conditions: (i) 2-methylcyclohexanone (0.01 mol), approp. aldehyde (0.01 mol) malononitrile (0.01 mol), NH4OAc (0.08 mol) in Abs. EtOH (50 mL), reflux 3–6 h; (ii) approp. starting compd. (0.01 mol), formic acid (5 mL), heated in boiling water bath 30 min; (iii) approp. starting compd. (0.01 mol), Ac2O (5 mL), conc. H2SO4 (0.5 mL), heated in boiling water bath 10 min; (iv) approp. starting compd. (0.01 mol), PhNCS (0.01 mol) in pyridine (15 mL), reflux 2 h; (v) approp. starting compd. (0.02 mol), PhCONCS (0.02 mol), dry acetone (10 mL), reflux 3 h; (vi) approp. thioureido deriv. (0.02 mol), 1N NaOH (5.5 mL), EtOH (10 mL), heated in boiling water bath 30 min; (vii) approp. starting compd. (0.001 mol), urea or thiourea (0.005 mol), fused at 260–300 °C, sand bath 1 h; (viii) approp. starting compd. (0.001 mol), urea or thiourea (0.005 mol), heated in microwave reactor at 250 °C, 15 min; (ix) approp. thione (0.02 mol), 1N NaOH (5 mL), EtOH (2 mL), alkyl or aralkyl halide (0.022 mol), stirred at r.t., 2–3 h and (x) approp. starting compd. (0.01 mol), HCONH2 (10 mL), reflux, 2–3 h.

Figure 1. 1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]thiourea.

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Synthesis and biological evaluation of some novel tetrahydroquinolines as anticancer and antimicrobial agents

Table 1. Physicochemical and analytical data of compounds 1–28.

Table 2. Physicochemical and analytical data of the scheme 2 compounds 29–51.

Table 3. ¹H NMR data of compounds 1–51.

Table 4. Cytotoxic effects (LC₅₀; μM)^a of the active compounds on some human tumor cell lines using the MTT assay.

Table 5. Minimal inhibitory concentrations [MIC, µg/mL (μM)] of the tested compounds.

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Synthesis and biological evaluation of some novel tetrahydroquinolines as anticancer and antimicrobial agents

Figures & data

Table 1. Physicochemical and analytical data of compounds 1–28.

Table 2. Physicochemical and analytical data of the scheme 2 compounds 29–51.

Table 3. 1H NMR data of compounds 1–51.

Table 4. Cytotoxic effects (LC50; μM)a of the active compounds on some human tumor cell lines using the MTT assay.

Table 5. Minimal inhibitory concentrations [MIC, µg/mL (μM)] of the tested compounds.

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Table 3. ¹H NMR data of compounds 1–51.

Table 4. Cytotoxic effects (LC₅₀; μM)^a of the active compounds on some human tumor cell lines using the MTT assay.