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[This corrects the article DOI: 10.1021/acsomega.9b02604.].

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A novel series of 1-amino-2-substituted-5-piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a-e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate, 2-bromoacetophenone, chloroacetamide, and chloroacetanilide. Construction the pyrrolyl ring associated with the thienotetrahydroisoquinoline moiety was achieved by treatment of compounds 4a, b with 2,5-dimethoxytertahydrofuran in acetic acid. 1-Pyrrolyl-2-substituted-thieno[2,3-c]isoquinolines 5a and 5b which in turn were used as multipurpose precursors for synthesis of other new heterocycles. Assignments of the chemical structures of the respectively synthesized thienotetrahydroisoquinolines and their derivatives were established on the bases of elemental and spectral techniques (Fourier transform infrared, 1H NMR, 13C NMR, and mass spectroscopy). Furthermore, certain compounds were screened for their antimicrobial activity which revealed promising activities against various pathogenic strains of bacteria and fungi.

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Neonicotinoids are the most widely used from all existing pesticides. So, in purpose to discover new pesticides being more effective against the aphid, twelve heterocyclic compounds neonicotinoid analogs have been prepared in a pure state; pyrimidothienotetrahydroisoquinolines 1-12 and their toxicity as potential insecticidal agents against cowpea Aphid, Aphis craccivora Koch was screened. Their characterizations by using spectroscopic analyses were performed. The toxicity data exhibited that the 8-chloropyrimidine compound 4 is more toxic about 2-fold than a reference insecticide, acetamiprid. The other screened compounds showed weak to strong toxicological activities against cowpea aphid.

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A new method for synthesizing 4-amino-3-methyl-1-phenyl-1H-5-substituted thieno[2,3-c]pyrazole was reported. The substituted groups at position 5 include carbonitrile, carboxamide, N-phenyl carboxamide, and benzoyl groups. The newly synthesized compounds and their derivatives were characterized by elemental analysis and spectroscopy (IR, 1H NMR, and mass spectra). Furthermore, some of these synthesized compounds were screened against various pathogenic bacterial and fungal strains. The results demonstrate that most of the synthesized compounds possess a significant antibacterial activity against gram-positive and gram-negative bacteria. In addition, most of these compounds showed a remarkable anti-fungal activity. On the other hand, some of the synthesized compounds possess high anti-inflammatory activity, which was demonstrated using the carrageenan-induced rat paw edema assay.

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Synthesis of bi functionally substituted thieno[2,3-c]pyrazole compounds was carried out by a new method. The substituted group at position five is namely (carbonitrile, carboxamide, N-(substitutedphenyl) carboxamide and benzoyl group). Chloroacetylation of the amino thieno[2,3-c]pyrazolecarboxamide compound afforded the chloroacetyl amino derivative. The chemical structure of the newly synthesized compounds was established by elemental and spectral analysis including IR, 1H NMR spectra in addition to 13C NMR and mass spectra for most of them. In the present work, we assessed the role of the new synthesized thieno[2,3-c]pyrazole compounds as antioxidants against the toxicity of the 4-nonylphenol on the red blood cells of the most economically important Nile fishes namely African catfish (Clarias gariepinus). The erythrocytes alterations were used as biological indicators to detect those effects. After exposure to 4-nonylphenol, the erythrocytes malformations (swelled cells, sickle cells, tear drop like cells, acanthocytes, and vacuolated cells) were recorded in highest number in comparison with other groups control and those injected with thieno[2,3-c]pyrazole compounds. So, the new thieno[2,3-c]pyrazole compounds can be used as antioxidants against toxicity of 4-nonylphenol on fishes.

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Reaction of 4-chlorocoumarin-3-carbonitrile with ethyl thioglycolate and ethyl glycinate hydrochloride leads to a series of title products. Hydrazinolysis of amino thienocoumarin carboxylate afforded the hydrazine derivative which underwent various reactions to build new heterocyclic rings containing thienocoumarin moiety. Chloro acetylation of aminoester compound afforded the chloro acetyl amino which underwent nucleophilic substitution reactions various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of Ghloroacetylamino with potassium thiocyanate yielded ethylpyrimidothieno coumarin sulfanylacetate which was used as a versatile precursor for synthesis of other heterocycles. On the other hand, reaction of chloro coumarin carbo nitrile with hydrazine gave the aminopyrazolocoumaine which reacted with bifunctionally compounds to give the substituted pyrimido derivatives. Diazotization and coupling of aminopyrazole with ethylcyanoacetate yielded ethylaminotriazinopyrazolocoumarine carboxylate. Several of the compounds obtained demonstrated considerable antifungal and antibacterial activity in the in vitro test systems.

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The acetyl benzo[f]coumarin condensed with phenyl hydrazine to afford the corresponding phenyl hydrazone which cyclized into the pyrazolyl benzocoumarin under Vilsmeier reaction conditions. The pyrazolylaIdehyde was used as starting material for synthesis of other heterocyclic compounds containing pyrazolylbenzocoumarin moiety. The ethyl benzo[f]coumarin carboxylate were subjected to react with other reagents to synthesize thiazolidinyl and oxadiazolyl derivatives attached to benzocoumarin system. Some of novel synthesized compounds showed highly antibacterial and antifungal activities.

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1-hydrazino-3-thioxo-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (3) was subjected to react with bifunctional compounds namely: acetylacetone, ethyl cyanoacetate, ethyl benzoylactate, diethylmalonate and ethyl acetoacetate to produce pyrazololthienotetrahydroisoquinoline derivatives 6-11. Also, heating of compound (3) with formic acid afforded triazolothienotetrahydroisoquinoline compound 5 which reacted with α-halogenated compounds to afford compounds 13a-e. Compound 13c when heated with triethylorthoformate afforded triazolo derivative 14. Also, compound 6 was used for synthesizing compounds 18-20. Representative compounds of the synthesized triazolo and pyrazolothienotetrahydroisoquinoline products were tested and evaluated as antimicrobial agents.

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