Synthesis and biological evaluation of fatty imidazolines

Satyavani, T.; Mohini, Y.; Karuna, Mallampalli Sri Lakshmi; Kumar, C. Ganesh; Poornima, M.; Sujitha, Pombala

doi:10.1007/s00044-014-0936-x

Cited by 4 publications

(5 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The group of sachalinols are secondary metabolites of the perennial herbaceous plant Rhodiola rosea (golden root) and Rhodiola sachalinensis . , Sachalinol A ( 55 ) was first described by the group of Kadota in 2001 . The strong cytotoxic property and good anticancer activity make Sachalinol A ( 55 ) an attractive synthetic target. Rosiridol ( 56 ) is the aglycone of the MAO inhibitor rosiridin and thus also a synthetically valuable target .…”

Section: Resultsmentioning

confidence: 99%

“…15a , 17 Sachalinol A ( 55 ) was first described by the group of Kadota in 2001. 15a The strong cytotoxic property and good anticancer activity 18 make Sachalinol A ( 55 ) an attractive synthetic target. Rosiridol ( 56 ) is the aglycone of the MAO inhibitor rosiridin and thus also a synthetically valuable target.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, the applicability of our protocol in convergent synthesis planning was impressively demonstrated by the total synthesis of two monoterpenoids. Thus, to the best of our knowledge, our synthesis of sachalinol A ( 55 ) represents the shortest synthesis of this cytotoxic compound to date. , Accordingly, this protocol of the Hoppe–Matteson–Aggarwal chemistry represents a synthetically very valuable alternative to the NHTK reaction.…”

Section: Discussionmentioning

confidence: 99%

“…Thus, to the best of our knowledge, our synthesis of sachalinol A ( 55 ) represents the shortest synthesis of this cytotoxic compound to date. 18 , 24 Accordingly, this protocol of the Hoppe–Matteson–Aggarwal chemistry represents a synthetically very valuable alternative to the NHTK reaction.…”

Section: Discussionmentioning

confidence: 99%

See 3 more Smart Citations

1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols

Linne,

Lohrberg,

Struwe

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki–Hiyama–Takai–Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe–Matteson–Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

See 2 more Smart Citations

1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols

Linne,

Lohrberg,

Struwe

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…In view of the increased threat from these drugresistant Gram-positive and Gram-negative bacterial strains and also Candida strains, there is a continuous demand and perusal to identify new antimicrobial agents. Several reports claim that numerous potent biological activities such as, insect repellent 3 , antibacterial [4][5][6][7] , pesticidal 8 , antifungal [9][10][11] , anti-inflammation 12 , antioxidant…”

Section: Introductionmentioning

confidence: 99%

Untitled

2016

IJPSR

View full text Add to dashboard Cite

A series of novel cholesteryl lactate-fatty acid conjugates (4a-i) were prepared by esterification of cholesterol with lactic acid, followed by coupling hydroxyl group of cholesteryl lactate with -COOH group of fatty acids including, saturated fatty acids of varying carbon chain of C 10 -C 18 , unsaturated fatty acids like 10-undecenoic, oleic ((9Z)-octadec-9-enoic), ricinoleic ((9Z,12R)-12-hydroxyoctadec-9-enoic) and 11-bromoundecanoic acid. Cholesteryl lactate-fatty acid conjugates were characterized by spectroscopic techniques like FT-IR, 1H-NMR, 13C-NMR, ESI-MS and HRMS. All the synthesized compounds were tested for their antimicrobial activity against a panel of seven bacterial strains like Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, Micrococcus luteus MTCC 2470, Klebsiella planticola MTCC 530, Escherichia coli MTCC 739, Pseudomonas aeruginosa MTCC 2453 and fungal strain like Candida albicans. Among them, the compounds with unsaturation (4f and 4h), and functional groups like bromine and hydroxyl group (4g and 4i) showed good antibacterial activity. But, promising activity was observed against Staphylococcus aureus MTCC 96 strain ranging from 7.8-15.6 µg/ml. These compounds (4f-i) are also exhibited good to moderate antifungal activity against different Candida strains ranging between 7.8-31.2 µg/ml.

show abstract