62756-19-8

Usage

Uses

Used in Fragrance and Flavor Industry:
Coumarine is utilized as a key ingredient in the fragrance and flavor industry due to its distinctive sweet scent. Its pleasant aroma makes it a valuable addition to perfumes, cosmetics, and food products, enhancing the sensory experience for consumers.
Used in Medicinal Chemistry and Drug Discovery:
Coumarine's potential anti-inflammatory, anti-cancer, and antioxidant properties have positioned it as a subject of interest in medicinal chemistry and drug discovery. Researchers are exploring its therapeutic potential for the development of novel treatments and pharmaceuticals.
Used in the Production of Blood Thinning Medications:
Leveraging its anticoagulant properties, coumarine is used in the production of blood thinning medications. These medications are essential for managing conditions such as deep vein thrombosis, pulmonary embolism, and atrial fibrillation, as well as preventing complications from certain surgeries.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 120-92-3 cyclopentanone 
• 86769-51-9 C₁₃H₁₃BrO₂ 
• 123-75-1 pyrrolidine 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 97207-24-4 3-Cyclopenten-1-ylchromon 
• 69-72-7 salicylic acid 
• 1630952-62-3 1-phenyl-8-(spiro[chroman-2,1'-cyclopentan]-4-yl)-1,3,8-triazaspiro[4.5]decan-4-one 
• 90878-16-3 2-(2-Cyclopentylidene-1-methyl-1-phenyl-ethyl)-phenol 
• 90878-15-2 2-(2-Cyclopentylidene-1-phenyl-ethyl)-phenol 
• 90-47-1 xanth-9-one 
• 70505-77-0 4-amino-2,2-tetramethylenechromane 

Relevant academic research and scientific papers

Development of a benzopyran-containing androgen receptor antagonist to treat antiandrogen-resistant prostate cancer

Antagonizing cancer 2 000 druglike small molecules were screened and a scaffold identified as a potentially novel androgen receptor antagonist framework. A focused library of 19 derivatives was then synthesized and evaluated in vitro against LNCaP prostate cancer cell line. A novel compound (6 f) was identified as a promising lead compound for the further development of new therapeutic agents against hormone-refractory prostate cancer.

Regioselective synthesis and through-space 13C-19F spin-spin coupling NMR of new tetracyclic 3-(trifluoromethyl)-spiro(chromen[4,3- c]pyrazole-4,1′-cycloalkanes)

This paper firstly describes an efficient and regioselective method for the synthesis of a new series of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2, 1′-cycloalkane)-3-yl]ethanones from spiro[chroman-2,1′-cycloalkan]- 4-ones (Kabbe's adduct). Yields o

Synthesis of novel trifluoromethyl-substituted spiro-[chromeno[4,3-d]pyrimidine-5,1′-cycloalkanes], and evaluation of their analgesic effects in a mouse pain model

Herein we report the synthesis of twelve 2,5-substituted 4-(trifluoromethyl)-spirochromeno[4,3-d]pyrimidines (7–10), as well as an evaluation of their analgesic effect in a mouse pain model. The nine new chromeno[4,3-d]pyrimidines (7–9) were synthesized f

Synthesis, biological evaluation and molecular docking study of 7-amine-spiro[chromeno[4,3-b]quinoline-6,1′-cycloalkanes] as new tacrine hybrids

This Letter reports the first series of seven examples of novel 7-amine-spiro[chromeno[4,3-b]quinoline- 6,1′-cycloalkanes], where cycloalkane is cyclopentane, cyclohexane, cycloheptane, 2-methyl-, 3-methyl-, 4-methyl-, and 4-t-butyl-cyclohexane. These new compounds were synthesized at yields of 30-65% by a one-pot cyclocondensation reaction of 2-aminobenzonitrile and seven examples of spiro[chroman-2,1′-cycloalkan]-4-ones, using AlCl3 as the catalyst, without solvent and under conventional thermal heating. Subsequently, these spirochromeno-quinolines were subjected to AChE and cytotoxicity activity, and molecular docking studies. Both results for these new tacrine analogues were correlated with the structural features and showed the best results for the tacrine hybrid that possesses the spirocyclopentane moiety.

New 1-(Spiro[chroman-2,1′-cycloalkan]-4-yl)-1H-1,2,3-Triazoles: Synthesis, QTAIM/MEP analyses, and DNA/HSA-binding assays

This study synthesized and characterized the DNA/HSA properties of a new series of 12 examples of 4-(alkyl/aryl)-1-(spiro[chroman-2,1′-cycloalkan]-4-yl)-1H-1,2,3-triazoles (SCTz), in which alkyl = CH3(CH2)5 and aryl = C6H5, 4-NH2C6H4, 3-OCH3C6H4 (47–95% yield) by regioselective Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) reaction. Additioanally, single crystal X-ray diffraction (SC-XRD) analysis was carried out and the SC-XRD data enabled a broad molecular analysis using QTAIM and MEP analysis. Absorption UV–Vis properties of SCTz series were investigated and all derivatives absorb in the UV region and no are observed emission fluorescence in solution. The DNA-binding assays (UV–Vis analysis) showed that the all spiroderivatives demonstrated strong binding forces to CT-DNA. The Stern-Volmer quenching constants (KSV) of SCTz were calculated and derivatives containing the OCH3 group competed more strongly with DNA minor grooves, followed by the increasing general order of (KSV): EB-DNA q) indicated a static interaction between spiroderivatives and DNA in all cases. Finally, the HSA-binding experiments and molecular docking studies for the new spiroderivatives were determined and quenching (KSV) and quenching rate (kq) constants values obtained for the SCTz suggest good interaction between HSA and derivatives, probably by static mechanism, forming HSA:compound adduct in the ground state.

Efficient approach for regioselective synthesis of new trifluoromethyl-substituted spirotetracyclic isoxazolines and isoxazoles

This paper describes firstly an effective protocol for the synthesis of a new series of five examples of 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1′-cycloalkan]-3-ols (4), in which the cycloalkanes — cyclopentane, cyclohexane, cycloheptane, and 4′-methyl- and 4′-t-butyl-cyclohexane — were isolated at yields of 65–84%. The dihydro-isoxazolinols 4 were obtained regioselectively from the reactions of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1′-cycloalkane)-3-yl]ethanones (3) with hydroxylamine hydrochloride, in the presence of sodium bicarbonate and methanol as solvent, for 24?h at 60?°C. The ethanone precursors 3 were synthesized by trifluoroacetylation reaction, employing trifluoroacetic anhydride and mixtures of enolethers and/or acetals derived from spiro[chroman-2,1′-cycloalkan]-4-ones (2) (Kabbe's adducts), which were obtained beforehand from the reaction of cycloalkanones 1 with 2-hydroxyacetophenone and pyrrolidine. Subsequently, dehydration reactions of isoxazolinols 4, employing thionyl chloride and pyridine, enabled the isolation of another series of five novel spiro-isoxazoles 5 (76–95% yield). The structural features of the two series of new spiro heterocycles (4 and 5) were unequivocally determined with the aid of: one-dimensional1H,13C, and19F NMR spectroscopy; two-dimensional1H and13C NMR spectroscopy (NOESY, gHMBC, and gHMQC); single crystal X-ray diffraction; and GC–MS.

An Efficient Synthesis of 6-oxa-spiro[3.4]octan-1-one Derivates Through 3-diazochroman-4-one and Alkene

Spiro[2,2-dimethyl-benzofuran,bicyclo [4.2.0]octane]-7′-one with fused and spirocyclic oxygen-containing rigid skeleton structure is obtained via Wolff rearrangement and cycloaddition with good yields. Then Spiro[2,2-dimethyl-benzofuran,hexahydro-isobenzofuran]-7′-one is synthesized by further Baeyer-Villiger oxidation. These two kinds of products have a special fused and spirocyclic oxygen-containing rigid skeleton structure and are reported by our group. (Figure presented.).

Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor

A series of triazospirodecanone derivatives were synthesized as potential NOP ligands. 8-(Chroman-4-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4) and its 5-fluoro analogue (18) proved to be active as agonists with EC50 values in the submicromolar range. Single enantiomers of compound 4 were separated and tested as NOP agonists; the eutomer R-(+)-4 showed a pEC 50 of 7.34. Finally docking studies were performed on the NOP receptor to identify the most significant stereospecific interactions.

Regioselective synthesis and through-space 13C-19F spin-spin coupling NMR of new tetracyclic 3-(trifluoromethyl)-spiro(chromen[4,3-c]pyrazole-4,1′-cycloalkanes)

This paper firstly describes an efficient and regioselective method for the synthesis of a new series of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1′-cycloalkane)-3-yl]ethanones from spiro[chroman-2,1′-cycloalkan]-4-ones (Kabbe's adduct). Yields of 38-61% were obtained when trifluoroacetylation reactions of mixtures of enolethers and/or acetals derived from four spiro ketones (Kabbe's adduct) were performed at a temperature of 45 °C, employing anhydrous chloroform as the solvent. Subsequently, when the respective trifluoroacetylated Kabbe adducts reacted with phenylhydrazine and methylhydrazine at a 1:1 molar ratio in refluxing ethanol for 24 h, a new series of seven examples of a new spiro-condensed heterocyclic system, namely 1(2)-methyl(phenyl)-3-(trifluoromethyl)-1,4(2,4)-dihydro-spiro(chromen[4,3-c]pyrazole-4,n′-cycloalkanes) - where cycloalkanes are cyclopentane, cyclohexane, and cycloheptane for n = 1; and tetrahydro-2H-pyran for n = 2 - were isolated at yields of between 35% and 51%. Finally, the structures of new spiro heterocycles were determined with the aid and simultaneous application of 1H, 13C and 19F one-dimensional and gHMBC NMR experiments, X-ray monocrystal diffraction, and mass spectrometry techniques.

Cycloadditions with 2,2-dialkyl-3-thioxochroman-4-one S-sulfides including an unprecedented [3 + 5] cycloaddition

We report the facile generation of the chroman-4-one-derived thiosulfines 10 under mild conditions by our well-established nucleophilic 'unzipping' of the corresponding acetyl α-chloroalkyl disulfides 9 which in turn can be prepared from the corresponding α-chloro sulfenyl chlorides 8. Spontaneous partial loss of sulfur from 10, most probably by the disproportionation of 10 to 11 and 12, generates the expectedly reactive β- oxo thioketones 11 which partly dimerize in a precedented Diels-Alder fashion, to give the 1,3,4-oxadithiins 13, and partly cycloadd to 10 to form the 1,2,4-trithiolanes 14 in a well-precedented fashion. Dimerization of 10 can occur in two competing ways: the precedented nonconcerted [3 + 3] cycloaddition (to give 1,2,4,5-tetrathianes 15) and the unprecedented concerted [3 + 5] addition to give 1,3,4,5,6-oxatetrathiocins 16. In the latter interaction one molecule of 10 behaves as a 1,5-dipole and a second molecule as a 1,3-dipole. In one case (10d) extensive sulfur scrambling takes place with formation of the 1,2,3,4,5,6-hexathiepane 17d. It is remarkable how sensitive the reactions of 10 are to minor variations of the simple alkyl substituents in the 2-position. In addition to the usual spectroscopic characterization all isolated key compounds were subjected to X-ray single- crystal structure determinations.