Stanimir Manolov

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• Doctor of Philosophy (PhD)
• Professor (Associate) at Plovdiv University

We report the synthesis of N-(2,2-diphenylethyl)furan-2-carboxamide. The compound was fully characterized by melting point determination, 1H and 13C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The combined analytical data confirm both the successful synthesis and the structural integrity of the target molecule.

Herein, we present the synthesis of N-(4-methoxyphenethyl)-2-oxo-2H-chromene-3-carboxamide. The synthesized compound has been thoroughly characterized using melting point analysis, ¹H- and ¹³C-NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The comprehensive data obtained from these techniques confirm the successful synthesis and st...

Herein, we report the synthesis of a series of new compounds by combining 2-aminobenzothiazole with various profens. The compounds were characterized using techniques such as ¹H- and ¹³C-NMR, FT-IR spectrometry, and high-resolution mass spectrometry (HRMS), with detailed HRMS analysis conducted for each molecule. Their biological activities were te...

A series of edaravone derivatives and the corresponding Cu(II) complexes were synthesized and characterized using spectroscopic and analytical techniques such as IR, UV, NMR and elemental analysis. Antioxidant activities of all compounds were examined using free radical scavenging methods such as hydrogen peroxide scavenging activity (HPSA), 1,1-di...

Herein we report the synthesis of three novel sulfonamide derivatives of trimetazidine—medication primarily used to treat angina pectoris. The new compounds have been fully characterized with their melting point, ¹H- and ¹³C-NMR, UV, and mass spectrometry. The collected data confirm the successful synthesis and structural integrity of the new molec...

Roman chamomile is a wild and cultivated plant in many countries worldwide and is mainly used in folk medicine. The flower's essential oil is used in various cosmetic, perfumery and aromatherapy products. In recent years in Bulgaria, the plant has been cultivated in the experimental field of the Institute of Roses, Essential and Medical Plants, Kaz...

In this study, we disclose the outcomes of the biological assessment of recently synthesized hybrids of ketoprofen with 2-phenylethylamines and 1,2,3,4-tetrahydroisoquinolines. These hybrids were obtained using an environmentally friendly method that minimizes the generation of waste products. The newly acquired hybrids were analysed to evaluate th...

In this study, we report the synthesis of (±)-2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide through the reaction of 7-amino-4-methyl-2H-chromen-2-one with (±)-2-chloro-2-phenylacetyl chloride. The in vitro anti-inflammatory activity of the new compound was evaluated, and the results indicated that it exhibited superior activity comp...

Isoquinoline alkaloids constitute a substantial category of natural products, among which 1,2,3,4-tetrahydroisoquinoline (THIQ) holds significance. THIQ-based compounds, whether natural or synthetic, showcase a wide array of biological activities, demonstrating efficacy against diverse infectious pathogens and neurodegenerative disorders. Consequen...

Mechanochemistry has emerged as a potential alternative for organic transformations, leveraging substrate availability, stability, and reduced solvent use. Its high efficiency and eco-friendly profile have garnered significant attention, particularly in the pharmaceutical industry, where it is hailed as the most promising environmentally friendly m...

Anise hyssop (Agastache foeniculum (Pursh) Kuntze) is a perennial plant belonging to the Lamiaceae family mainly used in folk medicine to treat various ailments. This study determined the chemical composition of the essential oil and evaluated its antimicrobial and antioxidant activity. The essential oil was obtained from plants cultivated in the e...

Herein, we report the synthesis of N-(3-chlorophenethyl)-4-nitrobenzamide in the reaction between 2-(3-chlorophenyl)ethan-1-amine and 4-nitrobenzoyl chloride. The newly obtained bio-functional hybrid molecule was fully characterized via ¹H, ¹³C NMR, UV, and mass spectral data.

In this study, we outline the eco-friendly mechanosynthesis of N-(2,2-diphenylethyl)-4-nitrobenzamide by reacting 2,2-diphenylethan-1-amine with 4-nitrobenzoyl chloride. The resulting bio-functional hybrid compound was meticulously characterized through the analysis of ¹H-, ¹³C-NMR, UV, and detailed mass spectral analysis.

In this study, we present the synthesis of five novel compounds by combining flurbiprofen with various substituted 2-phenethylamines. The synthesized derivatives underwent comprehensive characterization using techniques such as ¹H- and ¹³C-NMR spectroscopy, UV-Vis spectroscopy, and high-resolution mass spectrometry (HRMS). Detailed HRMS analysis wa...

This Special Issue of Processes, entitled “Synthesis, Application, and Biological Evaluation of Chemical Organic Compounds”, gathers the most recent work of leading researchers in a single forum [...]

Helichrysum italicum has piqued the interest of many researchers in recent years, mostly for its essential oil, but increasingly for its polyphenolic content as well. In the current study, we examine the polyphenolic composition of H. italicum grown in Bulgaria. The polyphenolic complex was fractionated with solvents of various polarities, includin...

Herein, we report the synthesis of 2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide in the reaction between 7-amino-4-methyl-2H-chromen-2-one and (±)-flurbiprofen. The newly-obtained bio-functional hybrid compound was fully characterized via ¹H, ¹³C NMR, UV, and mass spectral data.

The title compound, (±)-N-(1,2-bis(3,4-dimethoxyphenyl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide, was obtained for the first time from 1,2-bis(3,4-dimethoxyphenyl) ethan-1-amine and (±)-flurbiprofen in one step. The newly synthesized bio-functional hybrid compound was fully characterized using ¹H, ¹³C-NMR, UV, and mass spectral data.

Herein, we report the synthesis of four new hybrid molecules between ketoprofen or 2-(3-benzoylphenyl)propanoic acid and N-containing heterocyclic compounds, such as piperidine, pyrrolidine, 1,2,3,4-tetrahydroquinoline, and 1,2,3,4-tetrahydroisoquinoline. The obtained hybrid compounds were fully characterized using ¹H- and ¹³C-NMR, UV-Vis, and HRMS...

In the present work, we have investigated the polyphenolic composition of Chenopodium botrys from Bulgaria. The polyphenols were fractionated with solvents of varying polarity (n-hexane, chloroform, ethyl acetate, and n-butanol). The fractions were analyzed by HPLC-PDA and UHPLC-MS. The ethyl acetate fraction contained mono- and di-glycosides of qu...

Herein we report the synthesis of (±)-N-(3-chlorophenethyl)-2-(6-methoxynaphthalen-2-yl)propanamide in the reaction between 2-(3-chlorophenyl)ethan-1-amine and (±)-naproxen. The newly obtained bio-functional hybrid molecule was fully characterized via ¹H, ¹³C NMR, UV, IR, and mass spectral data.

The genus Nepeta, belonging to the family Lamiaceae, includes about 300 species, most of which are used in folk medicine due to their pronounced biological properties. The aim of the present study was to evaluate the agrobiological characteristics of Nepeta transcaucasica (N. transcaucasica) Grossh. and Nepeta cataria (N. cataria) L., cultivated in...

N-(3-chlorophenethyl)-2-(4-isobutylphenyl)propanamide was synthesized for the first time in the reaction between 2-(3-chlorophenyl)ethan-1-amine and 2-(4-isobutylphenyl)propanoyl chloride with high yield. The newly obtained chlorine-containing ibuprofen derivative was fully analyzed and characterized using ¹H-, ¹³C-NMR, UV, and mass spectral data.

Herein, we report the obtaining of new hybrid molecules of amphetamine with different profens (amfens). The obtained amfens are characterized by their melting points, UV, ¹H–, ¹³C–NMR, and HRMS spectra. A complete and detailed mass spectral analysis of the newly obtained derivatives of amphetamine with ibuprofen, flurbiprofen, ketoprofen, naproxen,...

Herein, we report the synthesis of new hybrid molecules between furan and N-containing heterocyclic compounds such as pyrrolidine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline, and piperidine. The obtained compounds were fully characterized using ¹H- and ¹³C-NMR, UV-Vis, and HRMS spectra. All compounds were assessed for their anti-in...

Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation acti...

2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide was synthesized by a reaction between amphetamine and flurbiprofen in high yields. The newly obtained hybrid molecule was fully analyzed and characterized via ¹H, ¹³C, UV, IR, HPLC, and mass spectral data.

Herein we report the biological evaluation of new hybrids of 1,2,3,4-tetrahydroisoquinoline with ibuprofen. The hybrids are screened for their in vitro inhibition of albumin denaturation, antioxidant, and antitryptic activity. The tested compounds have shown significant results. The lipophilicity was established using both reversed-phase thin layer...

Herein we report an eco-friendly method for the synthesis of 1,2,3,4-tetrahydroisoquinoline derivatives of ibuprofen. All five newly obtained compounds are fully characterized with their 1 H, 13 C-NMR, IR, HRMS, and are interesting for the purpose of studying their biological activities.

N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between benzo[d]thiazol-2-amine and flurbiprofen in high yield. The newly obtained flurbiprofen derivative was fully analyzed and characterized via ¹H, ¹³C, UV, IR, and mass spectral data.

N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide was prepared by a reaction between 2,2-diphenylethan-1-amine and naproxen in high yield. The newly obtained naproxen derivative was fully analyzed and characterized via ¹H, ¹³C, UV, IR, and mass spectral data.

Herein, we present the synthesis and in-vitro anti-inflammatory, antioxidant, and anti-arthritic activities of new ibuprofen derivatives. All structures were confirmed by spectral analysis (1 H NMR, 13 C NMR, UV, IR and HRMS). The lipophilicity was established using reversed-phase thin layer chromatography and in silico calculations. The anti-infla...

A new approach for the synthesis of Santacruzamate A analogues is demonstrated. The method allows functionalization at position 3 of the gamma-aminobutyric fragment and carbon chain variation.

The title compound was obtained in high yield in the reaction between tryptamine and naproxen. The newly synthesized naproxen derivative was fully analyzed and characterized via ¹H, ¹³C-NMR, UV, IR, and mass spectral data.

N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between tryptamine and flurbiprofen, applying N,N’-Dicyclohexylcarbodiimide, as a coupling agent. The obtained new amide has a fragment similar to Brequinar, a compound used in SARS-CoV-2 treatment trials. The newly synthesized compound was fully anal...

The influence of the duration of ultrasound-assisted extraction on antioxidant activity and total phenolics content of lupin seeds (Lupinus angustifolius L. cultivar 'Boregine') was investigated for the first time. Lupin seeds were of German origin but introduced in Bulgaria. They were extracted for 10, 20, and 30 min with absolute methanol, and th...

Herein we report an alternative eco-friendly method for the synthesis of 1,2,3,4-tetrahydroisoquinoline sulfonamide derivatives. All obtained compounds were screened for their in vitro inhibition of albumin denaturation, antioxidant, antitryptic, and antibacterial activity and have shown significant results. The lipophilicity was established using...

The titular compound was prepared by a reaction between tryptamine and carprofen, applying, as a “dehydrating” reagent, N,N’-dicyclohexylcarbodiimide. The newly synthesized compound was fully analyzed and characterized via ¹H, ¹³C-NMR, UV, IR, and mass spectral data.

Ketoprofen is a widespread non-steroidal anti-inflammatory agent used in treatment of acute pain and chronic arthritis. On the other hand, isoquinoline alkaloids are very well known with their wide range of biological activities. From this point of view it is of interest to us to obtain new isoquinolines containing a ketoprofen residue in their str...

Helichrysum italicum from the daisy family Asteraceae have been used in the folk medicine for many years for preventive purposes and for restoring the body after a heart attack. The plant material from H. italicum was provided by the Institute of Roses and Essential Oils, Kazanlak, Bulgaria. The antioxidant activity of different H. italicum extract...

The non-steroidal anti-inflammatory drugs (NSAIDs) are medications widely used to relieve pain, reduce inflammation, and bring down a high temperature. NSAIDs are used to relieve symptoms of headaches, painful periods, sprains and strains, colds and flu, arthritis, and other causes of longterm pain. We have used five members of the NSAIDs family as...

The compound in the title was prepared by reaction between tryptamine and ibuprofen using N,N′-dicyclohexylcarbodiimide as a “dehydrating” reagent. The structure of the newly synthesized compound was determined by nuclear magnetic resonance (NMR) (¹H-NMR and ¹³C-NMR), UV, IR, and mass spectral data.

It is known from the literature that ketoprofen is a widespread non-steroidal anti-inflammatory agent widely used in medical practice. On the other hand, isoquinoline alkaloids are also known to have a wide range of biological activities. That‘s why it is of interest to us to synthesize new isoquinoline compounds containing a ketoprofen residue in...

Smilyan beans are called bean seeds, one of the few Bulgarian foods protected by a trademark patent for its cultivation in the area of the upper valley of Arda River. Smilyan beans have a unique taste and are famous both in Bulgaria and abroad. Common beans (Phaseolus vulgaris L.) from two different cultivars from village of Smilyan were sieve anal...

Smilyan beans are called bean seeds, one of the few Bulgarian foods protected by a trademark patent for its cultivation in the area of the upper valley of Arda River. Smilyan beans have a unique taste and are famous both in Bulgaria and abroad. Common beans (Phaseolus vulgaris L.) from two different cultivars from village of Smilyan were sieve anal...

A simple, highly efficient, and eco-friendly method for obtaining

The compound named in the title was prepared from N¹,N⁴-diphenethylterephthalamide 1. The resulting bis terephthalamide was subjected to an intramolecular α-amidoalkylation reaction with paraformaldehyde in the presence of heterogeneous catalyst TfOH/SiO2 to obtain 1,4-phenylenebis[(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone]. The stru...

1,2,3,4-Tetrahydroisoquinolines are an important class of synthetic and natural compounds, which display a broad range of medicinal activities. The 1,2,3,4-tetrahydroisoquinoline system has attracted attention not only because of its biological activities, but also due to its presence as a basic framework in many naturally occurring products and dr...

1,2,3,4-Tetrahydroisoquinolines are an important class of synthetic and natural compounds, which display a broad range of medicinal activities. The 1,2,3,4-tetrahydroisoquinoline system has attracted attention not only because of its biological activities, but also due to its presence as a basic framework in many naturally occurring products and dr...

Synthetic studies of aryl-l,2,3,4-tetrahydroisoquinolines have attracted much attention from the synthetic community owing to the potential biological activities of this class of compounds and their increasing medicinal interest. The alkaloid cherylline is a naturally occurring optically active, 4-aryl-1,2,3,4- tetrahydroisoquinoline alkaloid, isol...

Tetrahydroisoquinolines are an important class of natural and synthetic compounds, which exhibit a vast range of biological activities, such as antitumor, antibacterial, antiplasmodial, and β-adrenergic receptor antagonism. Tetrahydroisoquinolines arylated at C-4 display prominent pharmaceutical activities. We report a microwave assisted α-amidoalk...

We report herein an application of an α-amidoalkylation reaction, as an alternative efficient synthesis of 4-aryl- and 4-methyl-1,2,3,4-tetrahydroisoquinoline derivatives. The amides required for this purpose would result from reaction of aminoacetaldehyde dimethylacetal with different substituted benzenes in polyphosphoric acid, followed by acylat...

The biological activity of isoquinoline derivatives, as analogues of various drugs, has provided great deal of interest for the synthesis of new compounds.An application of Bischler-Napieralski reaction for the synthesis of new 1,2,3,4-tetrahydroisoquinolines with biphenyl substituent on the 1st position and aryl substituent on 4th position, is des...

An application of α-amidoalkylation reaction, as an alternative efficient synthesis of analogues of cherylline, is reported. The required for this purpose amides would arise from reaction of aminoacetaldehyd-dimethylacetal with veratrole (1,2-dimetoxybenzene) in polyphosphoric acid, followed by acylation of obtained amines with different acid chlor...

The selective reduction of acylated b-enaminones under mild conditions, keeping enaminone moiety intact, is reported. The newly obtained compounds should be applied later for the synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines with potential anticonvulsic activity.

През Февруари и Март 2008 се проведе обмяна на студенти по физика и химия от Пловдивския университет и студенти по физика и химия от Университетите в Хелзинки и Юваскюла (Финландия) и университета в гр.Торун, Полша. Тя бе организирана по международен европейски проект за усъвършенстване на системата за провеждане на педагогическата практика на студ...