A Green Synthesis and a Chemical Study of the Coumarin, 1-(2-Hydroxy- 2-methyl-2H-chromen-3yl)ethanone

Coumarins are a class of natural and synthetic products with a wide variety of applications in different fields. Due to the general importance of coumarins, the objective of this work is to further develop the chemistry of 1-(2-hydroxy-2-methyl-2H-chromen-3yl)ethanone, 1, a potentially useful and versatile coumarin but an under-reported compound in the literature. This work describes a green preparation of 1 in the absence of solvents and acids, thereby eliminating byproducts, normally obtained in classical procedures, and a mechanistic study of the reactions of 1 with nucleophiles. In addition, we report the characterisation of 1-(2-ethoxy-2-methyl-2H-chromen-3-yl)ethanone 2, via X-ray crystallography and 2D NMR spectra.

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New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

Marine Drugs ◽

10.3390/md17030167 ◽

2019 ◽

Vol 17 (3) ◽

pp. 167 ◽

Cited By ~ 5

Author(s):

Pierre-Eric Campos ◽

Emmanuel Pichon ◽

Céline Moriou ◽

Patricia Clerc ◽

Rozenn Trépos ◽

...

Keyword(s):

Plasmodium Falciparum ◽

Minimum Inhibitory Concentration ◽

Marine Sponge ◽

Nmr Spectra ◽

Inhibitory Concentration ◽

Chemical Study ◽

2D Nmr ◽

Antimicrobial Activities ◽

2D Nmr Spectra ◽

Ic50 Values

Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.

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Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.14.280 ◽

2018 ◽

Vol 14 ◽

pp. 3011-3017

Author(s):

Akın Sağırlı ◽

Yaşar Dürüst

Keyword(s):

Nmr Spectra ◽

2D Nmr ◽

Synthetic Route ◽

X Ray ◽

H Nmr ◽

2D Nmr Spectra ◽

Tof Ms ◽

C Nmr

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, 1H NMR, 13C NMR, 2D NMR spectra, TOF–MS and X-ray measurements.

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Investigation of 8-Aza-7-Deaza Purine Nucleoside Derivatives

Molecules ◽

10.3390/molecules24050983 ◽

2019 ◽

Vol 24 (5) ◽

pp. 983

Author(s):

Hang Ren ◽

Haoyun An ◽

Jingchao Tao

Keyword(s):

Anticancer Activity ◽

Nmr Spectra ◽

2D Nmr ◽

Purine Nucleoside ◽

X Ray ◽

2D Nmr Spectra ◽

Purine Ring ◽

New Compounds

Glycosylation of 6-amino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine and its iodo- and bromo- analogues with the protected ribofuranose and 2′-deoxyribofuranose under different conditions resulted in the synthesis of N9- and N8-glycosylated purine nucleosides. Five key intermediate nucleosides, having 6-methoxy, 7-iodo, and 2-bromo groups, were further derivatized to 23 final 8-aza-7-deazapurine nucleoside derivatives. The structures of N9- and N8-glycosylated products were assigned based on UV and NMR spectra. HMBC analysis of 2D NMR spectra and X-ray crystallographic studies of the representative compounds unambiguously verified the connection of ribose ring to N9- or N8-position of the purine ring. The anticancer activity of these new compounds was evaluated.

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Osirisynes G-I, New Long-Chain Highly Oxygenated Polyacetylenes from the Mayotte Marine Sponge Haliclona sp.

Marine Drugs ◽

10.3390/md18070350 ◽

2020 ◽

Vol 18 (7) ◽

pp. 350 ◽

Cited By ~ 1

Author(s):

Pierre-Eric Campos ◽

Gaëtan Herbette ◽

Christophe Chendo ◽

Patricia Clerc ◽

Florent Tintillier ◽

...

Keyword(s):

Marine Sponge ◽

Active Compound ◽

Nmr Spectra ◽

Proteasome Inhibition ◽

Chemical Study ◽

2D Nmr ◽

Sirtuin 1 ◽

Fyn Kinase ◽

2D Nmr Spectra ◽

Long Chain

Chemical study of the CH2Cl2−MeOH (1:1) extract from the sponge Haliclona sp. collected in Mayotte highlighted three new long-chain highly oxygenated polyacetylenes, osirisynes G-I (1–3) together with the known osirisynes A (4), B (5), and E (6). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS and MS/MS data. All compounds were evaluated on catalase and sirtuin 1 activation and on CDK7, proteasome, Fyn kinase, tyrosinase, and elastase inhibition. Five compounds (1; 3–6) inhibited proteasome kinase and two compounds (5–6) inhibited CDK7 and Fyn kinase. Osirisyne B (5) was the most active compound with IC50 on FYNB kinase, CDK7 kinase, and proteasome inhibition of 18.44 µM, 9.13 µM, and 0.26 µM, respectively.

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Extensive 1D, 2D NMR Spectra of Some [7.0]Metacyclophanes and X-ray Analysis of (±)-Myricanol

Journal of Natural Products ◽

10.1021/np960230k ◽

1996 ◽

Vol 59 (8) ◽

pp. 759-764 ◽

Cited By ~ 20

Author(s):

Balawant S. Joshi ◽

S. William Pelletier ◽

M. Gary Newton ◽

Doowon Lee ◽

Georgia B. McGaughey ◽

...

Keyword(s):

Nmr Spectra ◽

2D Nmr ◽

X Ray ◽

2D Nmr Spectra

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Syntheses, Structures, and Spectroscopic Properties of Alkoxide, Hydroxide, and Siloxide Complexes with (η3-Allyl)Mo Moieties

Zeitschrift für Naturforschung B ◽

10.1515/znb-1999-0410 ◽

1999 ◽

Vol 54 (4) ◽

pp. 473-481 ◽

Cited By ~ 5

Author(s):

Cornelia Borgmann ◽

Christian Limberg ◽

László Zsolnai ◽

Katja Heinze

Keyword(s):

Solid State ◽

Low Temperature ◽

Single Crystal ◽

Nmr Spectra ◽

Room Temperature ◽

2D Nmr ◽

Spectroscopic Properties ◽

State Structure ◽

X Ray ◽

2D Nmr Spectra

Salts with binuclear anions of the general formula [(η3-C3H4R)(CO)2Mo(μ-OR′)2(μ-OR″)-Mo(CO)2(η3-C3H4R)]- (R = h , R′, R″ = Me, 2 ; R = CH3, R′ = CH(CH3)2, R″ = OH, 3; R = CH3, R′ = OH, R″ = OSiMe3, 4) have been synthesised via reaction of [(η3-C3H4R)- Mo(CO)2(CH3CN)2(thf)]+BF4- , 1, with NaOMe, NaOiPr, and KOSiMe3. All products were characterised spectroscopically and investigated by single crystal X-ray analysis. In the case of 3 low temperature 2D-NMR spectra revealed that the solid state structure is maintained in solution and that the compound shows a trigonal twist-rearrangement at room temperature.

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Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽

10.3390/md19010009 ◽

2020 ◽

Vol 19 (1) ◽

pp. 9

Author(s):

Ya-Ping Liu ◽

Sheng-Tao Fang ◽

Zhen-Zhen Shi ◽

Bin-Gui Wang ◽

Xiao-Nian Li ◽

...

Keyword(s):

Deep Sea ◽

Spectroscopic Data ◽

2D Nmr ◽

Penicillium Oxalicum ◽

Marine Phytoplankton ◽

Cold Seep ◽

Phytoplankton Species ◽

X Ray ◽

X Ray Crystallography ◽

Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

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Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽

10.3390/md19060305 ◽

2021 ◽

Vol 19 (6) ◽

pp. 305

Author(s):

Guangyuan Luo ◽

Li Zheng ◽

Qilin Wu ◽

Senhua Chen ◽

Jing Li ◽

...

Keyword(s):

Fusarium Solani ◽

2D Nmr ◽

Inflammatory Activity ◽

Raw264.7 Cells ◽

Spectroscopic Methods ◽

X Ray ◽

X Ray Crystallography ◽

Structure Activity ◽

Ic50 Values ◽

New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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