In this Short Note type article, we report the synthesis of a new hybrid molecule, N-(3,4-dimethoxyphenethyl)-2-propylpentanamide, using a solvent-minimized mechanochemical method that provides a simple and efficient synthetic approach. The process a...
Interest in non-centrosymmetric crystalline materials exhibiting second harmonic generation (SHG) has increased due to their potential applications in optical sensing and biosensing. Saccharide-based metal complexes are particularly attractive system...
Suzuki–Miyaura coupling of 3-chloro-5-[(2-ethylhexyl)amino]-4H-1,2,6-thiadiazin-4-one with phenylboronic acid, at ca. 100 °C, gave 3-[(2-ethylhexyl)amino]-5-phenyl-4H-1,2,6-thiadiazin-4-one in 69% yield. Another nucleophilic substitution re...
An alkene-tethered enaminone 7 was synthesized in four steps from bromoacetic acid and 3,3-dimethylallyl alcohol. The enaminone was fully characterized, including UV-Vis spectra. TBADT-catalyzed HAT of the alkene-tethered enaminone initiated a fragme...
Spirocyclic compounds are experiencing a research surge due to their unique 3D structure, offering enhanced pharmacological, industrial, and material applications. They are increasingly used in medicinal chemistry to improve drug-like properties, suc...
1,4-Dimethoxy-2,3-dinitrobenzene (1) reduction using sodium hydrosulfite resulted in 3,6-dimethoxybenzene-1,2-diamine (2) and 3,6-dimethoxy-2-nitroaniline (3) in 24% and 59% yields, respectively. Nitroaniline 3 was acetylated with acetyl chloride to...
Owing to their distinctive physicochemical features, their structural analogues of benzene ring bioisosteres, and their strong affinity for biomacromolecules, pyridine derivatives function both as core structural scaffolds in pharmacologically active...
This study investigates the rational design of a dinuclear zinc(II) coordination polymer, (C36H34Br2N8O4S2Zn2), to explore how halogen substitution and ligand choice modulate structural architecture, contributing to the development of functional coor...
An effective one-step synthetic procedure for preparation of hydroxylated analogues of ethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate as novel promising multifunctional building blocks for drug discovery based on the Gewald procedure...
The reaction of 4,4-dimethyl-8-(4-methylbenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with thioacetamide in a 1:1 ratio when refluxed in dichloromethane gives (4S*,10aS*,11S*)-4-hydroxy-2,7,7-trimethyl-11-(4-methylbenzoyl)-7,8-dihyd...
A DABCO-catalyzed one-pot synthesis of a novel pentacyclic heterocycle featuring an unprecedented benzo[4,5]imidazo[1,2-a]chromeno[3,2-e]pyridine scaffold from 2-(cyanomethyl)benzimidazole and 3-trifluoroacetyl-4-phenyl-4H-chromene has been developed...
The synthesis of methyl (E)-3-(2-amino-4-chloro-6-morpholinopyrimidin-5-yl)acrylate 3 was accomplished using a Schlosser-modified Wittig reaction. Complete 1H and 13C NMR signal assignments confirm the formation of E-alkene.
In this report, we describe the synthesis and full spectroscopic characterization of a previously unreported podophyllotoxin (PTOX) analogue bearing a second 3,4,5-trimethoxyphenyl (TMP) unit at the C-4 position through an ester linkage. This dual-TM...
Peri-substituted bis(tertiary) phosphine-arsine Acenap(PiPr2)(As(SPh)Ph) (4, Acenap = acenaphthene-5,6-diyl) was synthesized by the reaction of the chloroarsine (PiPr2)(AsPhCl) with PhSLi. The X-ray crystal structure of this compound reveals an intra...
Vinylimidazolium salts constitute a highly relevant class of polymerizable heterocycles, especially in the field of so-called polymer ionic liquids (PILs), and they are frequently used as components of polyelectrolytes. Therefore, crystallographic ch...
As a part of an SAR study aimed at testing the antitumor activity of some C15 acetogenins related to mycalin A, we report here the synthesis of the C-1 debromo-derivative of laurenciallene, a substance recently isolated from the red alga Laurencia ob...
Here, we synthesized 2,3,4,6-tetra(9H-carbazol-9-yl)benzonitrile (4CzHPN) via visible-light-driven photocatalytic monodecyanation using the versatile metal-free catalyst 4CzIPN. Characterized by NMR, IR, X-ray diffraction, and DFT calculations, it fe...
The title compound 2-iodopyridin-3-yl acetate was obtained by acetylation of the OH group of 2-iodo-3-hydroxypyridine. Knowing that the hydroxyl group, as a strong H-bond donor in halogenated hydroxypyridines, usually directs supramolecular packing a...
The previously unknown compounds—3-(dichloromethyl)-2-nitro-6,7-dihydro-1-benzofuran-4(5H)-ones—have been synthesized and structurally characterized via single-crystal X-ray diffraction, 1H, 13C–{1H}, 1H–13C HMQC and 1H–...
Indane-1,3-dione and 1,4-dihydropyridine (1,4-DHP) scaffolds are of significant interest in medicinal chemistry. Herein, we report the synthesis characterization of a new lipid-like indane-1,3-dione–1,4-DHP betaine, 2-(3′,5′-bis((do...
Herein, we report the mechanochemical synthesis of a novel hybrid molecule, N-(4-methoxyphenethyl)-2-propylpentanamide. This solvent-minimized synthesis aligns with the principles of Green Chemistry and exemplifies the emerging paradigm of medicinal...
We report the crystallization and single-crystal X-ray analysis of the monohydrate hydrochloride salt of chloroquine(CQ), abbreviated CQHCl·H2O, an antimalarial drug with the formula C18H26ClN3. The crystal structure reveals a well-defined sup...
(2RS,3aRS,9aRS)-3a-methyl-2-phenyl-3,3a,9,9a-tetrahydro-1H-benzo[f]indol-4(2H)-one hydrobromide was first synthesized via a tandem aza-Cope rearrangement and Mannich reaction from (1RS,2SR)-2-amino-1-(prop-1-en-2-yl)-2,3-dihydro-1H-inden-1-ol, which,...
The addition of 3-isocyanatopropyltriethoxysilane and 2-aminonaphthalene in THF affords the title compound 1-(naphthalen-2-yl)-3-(3-(triethoxysilyl)propyl)urea 1. A determination of the crystal structure of this naphthyl urea reveals the occurrence o...
2-({3-[2-(1-cyclohexen-1-yl)ethyl]-6,7-dimethoxy-4-oxo-3,4-dihydro-2-quinazolinyl}sulfanyl)-N-(4-ethylphenyl)butanamide (K284-6111; K284), the representative CHI3L1 inhibitor, has interesting biological activities, including anti-cancer and anti-infl...
This study presents the synthesis of a new compound, ethyl 2-(2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazinyl)thiazole-4-carboxylate, obtained by the Hantzsch heterocyclisation reaction. The compound was analyzed through melting point determi...
A phytochemical investigation of Myristica ceylanica resulted in the identification of seven arylalkanone-derived phenolic compounds, comprising one new naturally occurring arylalkanone (A), two derivatives (A1 and A2) prepared by chemical synthesis,...
Reactions of 3′,5′-dichlorospiro(benzo[d][1,3]dioxole-2,4′-[1,2,6]thiadiazine) or 6,10-dichloro-1,4-dioxa-8-thia-7,9-diazaspiro[4.5]deca-6,9-diene with ammonia in MeCN, at ca. 20 °C, gave 5′-chlorospiro(benzo[d][1,3]dioxol...
Overexpression of protein phosphatase 5 (PP5) is implicated in tumor cell growth, establishing PP5 as a compelling target for small-molecule anticancer therapy. Building on prior success in achieving selectivity within the PP2A domain through scaffol...
Herein we describe the synthesis of N-(2-(1H-indol-3-yl)ethyl)-2-propylpentanamide. The compound was comprehensively characterized using melting-point analysis, 1H and 13C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The collective...
A symmetrical rubrene derivative, 5,6-bis(4-(methoxycarbonyl)phenyl)-11,12-diphenyltetracene, was synthesized via the thermal dimerization of 1,1-diphenyl-3-[4-(methoxycarbonyl)phenyl]-3-chloroallene. The reaction proceeded with the low selectivity t...
A novel unsymmetrical azine, 6-((2-oxoindolin-3-ylidene)hydrazineylidene)indolo[2,1-b]quinazolin-12(6H)-one, was synthesized through a condensation reaction between tryptanthrin-6-hydrazone and isatin in chloroform under reflux conditions. Structural...
A cyclometalated platinum(II) complex [Pt(bzq)(BINAP)]PF6 bearing a 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) auxiliary ligand and a cyclometalated benzo[h]quinoline (bzq) ligand have been prepared. Structural characterizatio...
We report an efficient and transition-metal-free protocol for the propargylation of 4-(4-chlorophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile using propargyl bromide in the presence of cesium carbonate in dimethylsulfoxide under mild condi...
The 1,4-dipolar cycloaddition of the ylidene derivative of 1H-pyrrole-2,3-dione to a dipole generated in situ from 1-benzylbenzimidazole and dimethyl acetylenedicarboxylate proceeds via the exocyclic multiple bond of the ylidene derivative and afford...
The reaction of aliphatic aldehydes with the tautomers 6,6-dimethyl-4-hydroxy-2H-thiopyrane-2-thione and 6,6-dimethyl-2-mercapto-4H-thiopyrane-4-one is reported to yield spiro compounds. However, the spiro compound of the reaction with formaldehyde i...
A novel spiro-pyrrolothiazole derivative bearing a 2-oxindole substituent was synthesized and characterized. The compound was prepared via a catalyst-free reaction under mild conditions and isolated using a straightforward workup procedure. The struc...
A cone calix[4]arene having one tert-butyl group and three amino groups at the wide rim was bis-N-protected stepwise using sulfonylation with 4-nitrobenzylsulfonyl chloride, followed by acylation with di-tert-butyl dicarbonate. The selective sulfonyl...
Herein, we present the synthesis of N-(3-methoxyphenethyl)-2-propylpentanamide, a derivative of valproic acid. The compound has been thoroughly characterized through melting-point determination, 1H and 13C NMR spectroscopy, infrared spectroscopy, and...
Benzyl 2,4-dichlorophenyl sulfoxide was synthesized both in racemic and in an enantiopure form. This enantiopure sulfoxide is a further successful confirmation of our straightforward protocol to yield easily chiral aryl benzyl sulfoxides. We solved a...
In 2019, carbamates derived from 3-hydroxypyridine were classified as nerve agents and subsequently included in the Annex on Chemicals by the Conference of the States Parties. Herein, we describe the preparation of a structural simulant of this class...
Perimidine derivatives are versatile heterocycles with growing significance in medicinal chemistry and materials sciences. However, their structural variety remains limited. This study focused on the synthesis and crystal structure characterization o...
Friedelin, a pentacyclic triterpene, has been reported to inhibit potential reactive oxygen species (ROS)-scavenging activity. Accordingly, we modified the structure of this compound with the aim of obtaining derivatives. A new derivative (compound 4...
We report the first synthesis of 3,5-diamino-substituted dithieno[3,2-b:2′,3′-d]thiophene derivatives, bearing alkoxycarbonyl or acetyl groups at C-2 and C-6 positions. The target compounds were prepared via the reaction of 3,4-dibromothi...
(S)-2-methyl-5-(prop-1-en-2-yl)cyclopent-1-ene-1-carbaldehyde (2) is a component of the essential oils of several plants and has also been used in many syntheses, usually of terpenes. Although the preparation of compound 2 has been reported several t...
1β, 6α-dihydroxy-5αH-eudesma-3(4), 11(13)-dien-12, 8β-olide is a natural eudesmane sesquiterpene lactone isolated from the aerial parts of Inula nervosa Wall. In this paper, we report the X-ray crystallography of the compound 1...
The multicomponent synthesis of a novel and highly symmetric polyheterocycle based on the pyrrolo[3,4-b]pyridin-5-one core incorporating the privileged tetrahydroisoquinoline moiety is described. The target compound was synthesized as an inseparable...
Compounds based on the pyrazoloquinazoline scaffold are of significant interest in synthetic organic chemistry owing to their potential biological activity. In this work, we describe the synthesis of a new derivative with this scaffold, 9-oxo-2-(p-to...
We report the synthesis and molecular structure as determined by single-crystal X-ray diffraction of P,P,P′,P′-tetraisopropyl(1,4-phenylenebis(hydroxymethylene))bis(phosphonate). The compound was fully characterized by 1H, 13C, and 31P NM...
Substituted thiourea derivatives represent a structurally diverse group of compounds with high biological activity. In this paper, we present the synthesis of N-(9-ethyl-9H-carbazol-2-yl)-N′-(1-phenylethyl)thiourea by condensation reaction. The...
