Detailed 1H and 13C NMR structural assignment of three biologically active lignan lactones

A new type of herbicides based on imidazolinones has been introduced into agriculture under commercial names of Arsenal, Pursuit, Scepter, Assert etc. by American Cyanamid Company since 1983. These compounds destroy diocotyledonous weeds and are almost nontoxic for mammals and fish (LD50 rat - 500 mg/kg, LD50 trout - 300 mg/kg) and nonmutagenic according to the AMES test. The aim of the present work is to synthesize substituted 2-benzoylaminocarboxamides as starting materials for preparation of imidazolinones and potential biologically active substances (Formulae I - III).

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Synthesis of some biologically active 2,4'-bipyridine-5-carbonitriles carrying the 4-hydroxyphenylthio moiety

Journal of the Serbian Chemical Society ◽

10.2298/jsc0907733k ◽

2009 ◽

Vol 74 (7) ◽

pp. 733-743 ◽

Cited By ~ 1

Author(s):

T. Karabasanagouda ◽

Vasudeva Adhikari ◽

G. Parameshwarappa

Keyword(s):

13C Nmr ◽

Ammonium Acetate ◽

Ethyl Cyanoacetate ◽

Aromatic Aldehydes ◽

Biologically Active ◽

The Other ◽

Mass Spectral Data ◽

1H And 13C Nmr ◽

Mass Spectral

A series of new 4-aryl-2'-[(4-hydroxyphenyl)thio]-6oxo-1,6-dihydro- 2,4'-bipyridine-5-carbonitriles (3a-k) and 6-amino-4aryl-2'-[(4-hydroxyphenyl) thio]-2,4'-bipyridine-5-carbonitriles (4a-h) were synthesized from 4-hydroxythiophenol (1). The reaction of 4-hydroxythiophenol with 4-acetyl-2-chloropyridine yielded 1-{2-[(4-hydroxyphenyl)thio]pyridin-4-yl}ethanone (2). Further treatment of 2 with ethyl cyanoacetate in the presence of ammonium acetate with various aromatic aldehydes furnished the compounds 3a-k. On the other hand, condensation of 2 with aromatic aldehydes in the presence of alcoholic malononitrile in ammonium acetate gave compounds 4a-h. The structures of the newly synthesized compounds were established on the basis of their elemental analysis, as well as their IR, 1H- and 13C-NMR and mass spectral data. All the title compounds were subjected to in vitro antibacterial testing against two strains and antifungal screening against two fungi. Some of the compounds showed promising activity.

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1H and 13C NMR spectral assignments of the major sequences of twelve systematically modified heparin derivatives

Carbohydrate Research ◽

10.1016/s0008-6215(96)00213-3 ◽

1996 ◽

Vol 294 (1-4) ◽

pp. 15-27 ◽

Cited By ~ 40

Author(s):

E Yates

Keyword(s):

13C Nmr ◽

1H And 13C Nmr ◽

Heparin Derivatives

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Some Considerations Regarding the 1H and 13C Spectra of 4-(1-azulenyl)-2,6-bis(2-heteroaryl-vinyl)- pyrylium and Pyridinium and their Corresponding Pyridines

Revista de Chimie ◽

10.37358/rc.18.1.6045 ◽

2018 ◽

Vol 69 (1) ◽

pp. 64-69

Author(s):

Liviu Birzan ◽

Mihaela Cristea ◽

Constantin C. Draghici ◽

Alexandru C. Razus

Keyword(s):

Double Bond ◽

13C Nmr ◽

Nmr Spectra ◽

Chemical Shifts ◽

Pyridinium Salts ◽

13C Nmr Spectra ◽

1H And 13C Nmr ◽

Pyrylium Salts

The 1H and 13C NMR spectra of several 2,6-diheteroarylvinyl heterocycles containing 4-azulenyl moiety were recorded and their proton and carbon chemical shifts were compared with those of the compounds without double bond between the heterocycles. The influence of the nature of central and side heterocycles, molecule polarization and anisotropic effects were revealed. The highest chemical shifts were recorded for the pyrylium salts and the lowest at pyridines, but in the case of the pyridinium salts, the protons chemical shifts at the central heterocycle are more shielded due to a peculiar anisotropy of the attached vinyl groups.

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Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

Letters in Organic Chemistry ◽

10.2174/1570178616666190905142545 ◽

2020 ◽

Vol 17 (11) ◽

pp. 832-836

Author(s):

Manijeh Nematpour ◽

Hossein Fasihi Dastjerdi ◽

Mehdi Jahani ◽

Sayyed Abbas Tabatabai

Keyword(s):

13C Nmr ◽

Reaction Times ◽

High Yield ◽

One Pot ◽

1H And 13C Nmr ◽

Activation Reaction ◽

Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

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The Development of Tyrosyl-DNA Phosphodyesterase 1 (TDP1) Inhibitors Based on the Amines Combining Aromatic/Heteroaromatic and Monoterpenoid Moieties

Letters in Drug Design & Discovery ◽

10.2174/1570180816666181220121042 ◽

2019 ◽

Vol 16 (5) ◽

pp. 597-605 ◽

Cited By ~ 1

Author(s):

Evgenii Mozhaitsev ◽

Evgenii Suslov ◽

Yuliya Demidova ◽

Dina Korchagina ◽

Konstantin Volcho ◽

...

Keyword(s):

Dna Repair ◽

Tumor Cell ◽

13C Nmr ◽

Inhibitory Activity ◽

Secondary Amines ◽

Repair Enzyme ◽

1H And 13C Nmr ◽

Chemical Structures ◽

Natural Substances ◽

Micromolar Range

Background: Inhibition of the DNA repair enzyme, tyrosyl-DNA phosphodiesterase 1 (TDP1), may increase the efficacy of cancer drugs that cause damage to tumor cell DNA. Among the known TDP1 inhibitors, there are compounds containing moieties of natural substances, e.g., monoterpenoids. In this work, we synthesized several compounds containing aromatic/ heteroaromatic amines and monoterpenoid groups and assessed their TDP1 inhibition potential. Methods: Structures of all the synthesized compounds were confirmed by 1H and 13C NMR as well as HRMS. The TDP1 inhibitory activity of the amines was determined by real-time fluorescence oligonucleotide biosensor. Results: The synthesized secondary amines had TDP1 inhibitory activity IC50 in the range of 0.79-9.2 µM. The highest activity was found for (–)-myrtenal derivatives containing p-bromoaniline or m-(trifluoromethyl)aniline residue. Conclusion: We synthesized 22 secondary amines; of these, 17 amines are novel chemical structures. Many of the amines inhibit TDP1 activity in the low micromolar range. Therefore, these compounds are promising for further study of their antiproliferative activity in conjunction with DNA damaging drugs.

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8-Acyl-7-phenylbicyclo[2.2.2]-2,6-diones by rearrangement of 3-acyloxy-5-(2-phenylethenyl)-2-cyclohexen-1-ones. 1H and 13C NMR spectral evidence of their structure

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19901208 ◽

1990 ◽

Vol 55 (5) ◽

pp. 1208-1215 ◽

Cited By ~ 1

Author(s):

Pavel Hrnčiar ◽

Tibor Liptay ◽

Ján Šraga

Keyword(s):

Double Bond ◽

Spectral Data ◽

13C Nmr ◽

1H And 13C Nmr ◽

Spectral Evidence ◽

C Nmr

3-Acyloxy-5-(2-phenylethenyl)-2-cyclohexen-1-ones II were prepared by O-acylation of 5-(2-phenylethenyl)-1,3-cycloxanedione (I). Treatment of II with AlCl3 resulted in rearrangement of the acyl group to the double bond of the phenylethenyl grouping followed by cyclization to 8-acyl-7-phenylbicyclo[2.2.2]octane-2,6-diones III. Their structure was evidenced by analysis of the 1H and 13C NMR spectral data.

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(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽

10.3390/m1140 ◽

2020 ◽

Vol 2020 (2) ◽

pp. M1140

Author(s):

Jack Bennett ◽

Paul Murphy

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

Ir Spectroscopy ◽

13C Nmr ◽

Conjugate Addition ◽

13C Nmr Spectroscopy ◽

One Pot ◽

1H And 13C Nmr ◽

Esi Mass Spectrometry ◽

The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

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