Stereoselectivity of formation of monoterpene – Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives

Marenin, K. S.; Gatilov, Yu. V.; Agafontsev, A. M.; Ткачев, А. В.

doi:10.1016/j.steroids.2016.09.016

Cited by 3 publications

(2 citation statements)

References 43 publications

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“…Analysis of high‐field 2D 1 H‐ 1 H and 13 C‐ 1 H‐correlation NMR spectra of the products demonstrate that sets of proton and carbon chemical shifts and proton‐proton and carbon‐proton spin‐spin couplings for each compound are similar to those of the previously reported structurally relative terpene‐amino acids hybrids . Formation of α‐aminophosphonate moiety is proved by characteristic 1 H‐ 31 P and 3 C‐ 31 P spin‐spin couplings.…”

Section: Resultssupporting

confidence: 65%

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

et al. 2020

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Three-component condensation of aldehydes and dimethyl phosphite with α-amino oximes derived from (À)-α-pinene and (+)-3-carene (Kabachnik-Fields reaction) resulted in amino phosphonates as pairs of diastereomers. Diastereomeric ratio depends on the catalyst used (SnCl 2 × 2H 2 O, SiO 2 , Al 2 O 3-H +) and the heating type (conventional or microwave). The best results were achieved by MW irradiation with simultaneous cooling. Stereochemical assignment of the key derivatives was made by X-ray diffractometry. According to quantum chemical calculations (DFT PBE0/def2-TZVPP) and spectroscopic data, the terpenic α-amino phosphonates should be conformationally inhomogeneous, exhibiting a tendency to form H-bonded dimers (DFT M06/def2-SVP, IR). One-bond spin-spin coupling 1 J P-C was found to be diagnostic for the configuration assignment since the value 1 J P-C depends on the dihedral angle between bond CÀ P and axis of the electron lone pair at the neighboring nitrogen (NMR, DFT PBE0/aug-cc-pVTZÀ J).

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Section: Resultssupporting

confidence: 65%

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

et al. 2020

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“…Terpene hybrids reported in bibliography include hybrids between terpene-benzoylphenyl urea (BPU) [ 27 ], hybrid terpene-amino acid [ 28 , 29 ], hybrid terpene-quinone [ 17 , 30 ], hybrid terpene-anti-inflammatory agents [ 31 ], hybrid terpene-NSAID [ 32 ], among others. However, to date there is little information on the possible biological effect that hybrid molecules formed by the fusion of two different terpenes may have.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

et al. 2018

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Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.

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Copper(II) Complexes with Chiral Ligands Containing Fragments of Monoterpenoids and Amino Acid Esters

et al. 2018

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Stereoselectivity of formation of monoterpene – Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives

Cited by 3 publications

References 43 publications

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

Stereochemistry of the Kabachnik‐Fields Condensation of Terpenic Amino Oximes with Aldehydes and Dimethyl Phosphite

Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

Copper(II) Complexes with Chiral Ligands Containing Fragments of Monoterpenoids and Amino Acid Esters

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