Efficient hydrogenation of benzaldoximes and Schiff bases on ceramic high-porosity palladium catalysts

Игнатов, А В; Varakutin, Alexander E.; Solov'eva, I. N.; Karmanova, I. B.; Kozlov, I. A.; Semenova, Marina N.; Семенов, В. В.

doi:10.1007/s11172-018-2230-4

Cited by 6 publications

(2 citation statements)

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“…To analyze the importance of linker length and structure for antiproliferative activity, we developed synthetic procedures for the preparation of TPP-conjugated polyalkoxybenzene derivatives 11, 16, 17, and 22 with chain lengths of 6−8 atoms including ether, esteric, or amide groups from the corresponding aldehydes 8, intermediate phenol 9, 39 benzyl alcohol 12, 40 or benzyl amide 13 41 TPP conjugate 11 with the ether linker of seven atoms, we introduced a synthetic protocol that included alkylation of phenol 9 with an excess of dibromohexane followed by Ph 3 Pquaternization of intermediate bromide 10 (Scheme 2). Apiol−TPP derivatives featuring linkers of eight atoms with esteric (16) or amide (17) groups were synthesized by acylation of corresponding benzyl alcohol 12 or benzylamine 13 with 6-bromohexanoic acid followed by Ph 3 P-quaternization of intermediates 14 and 15 (Scheme 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…To analyze the importance of linker length and structure for antiproliferative activity, we developed synthetic procedures for the preparation of TPP-conjugated polyalkoxybenzene derivatives 11 , 16 , 17 , and 22 with chain lengths of 6–8 atoms including ether, esteric, or amide groups from the corresponding aldehydes 8 , intermediate phenol 9 , benzyl alcohol 12 , or benzyl amide 13 (Schemes and ). To obtain apiol–TPP conjugate 11 with the ether linker of seven atoms, we introduced a synthetic protocol that included alkylation of phenol 9 with an excess of dibromohexane followed by Ph 3 P-quaternization of intermediate bromide 10 (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

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Synthesis and Antiproliferative Activity of Triphenylphosphonium Derivatives of Natural Allylpolyalkoxybenzenes

et al. 2022

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Derivatives of natural allylpolyalkoxybenzenes conjugated to triphenylphosphonium (TPP) cations by aliphatic linkers of three, six, seven, and eight atoms were synthesized to examine the role of the polyalkoxybenzene pharmacophore, TPP fragment, and linker length in antiproliferative activities. The key synthetic procedures included (i) hydroboration−oxidation of apiol, dillapiol, myristicin, and allyltetramethoxybenzene; (ii) acylation of polyalkoxybenzyl alcohols or amines; and (iii) condensation of polyalkoxybenzaldehydes followed by hydrogenation and cyclopropyl−homoallyl rearrangement. The targeted TPP conjugates as well as the starting allylbenzenes, the corresponding alkylpolyalkoxybenzenes, and the respective alkyl-TPP salts were evaluated for cytotoxicity in a panel of human cancer cell lines using MTT and Click-iT-EdU assays and in a sea urchin embryo model. The linker of three carbon atoms was identified as favorable for selective cancer cell growth inhibition. Although the propyl-TPP salt was cytotoxic at low micromolar concentrations, the introduction of a polyalkoxybenzene moiety significantly potentiated inhibition of both cell growth and de novo DNA synthesis in several human cancer cell lines, HST-116 colon cancer, A375 melanoma, PC-3 prostate cancer, and T-47D breast carcinoma cells, while it failed to produce any developmental abnormalities in the sea urchin embryos.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…To analyze the importance of linker length and structure for antiproliferative activity, we developed synthetic procedures for the preparation of TPP-conjugated polyalkoxybenzene derivatives 11 , 16 , 17 , and 22 with chain lengths of 6–8 atoms including ether, esteric, or amide groups from the corresponding aldehydes 8 , intermediate phenol 9 , benzyl alcohol 12 , or benzyl amide 13 (Schemes and ). To obtain apiol–TPP conjugate 11 with the ether linker of seven atoms, we introduced a synthetic protocol that included alkylation of phenol 9 with an excess of dibromohexane followed by Ph 3 P-quaternization of intermediate bromide 10 (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%