Synthesis of arylated norbornyl amino acid esters

Günkara, Ömer Tahir; Kulu, İrem; Öcal, Nüket; Kaufmann, Dieter

doi:10.1007/s00706-010-0384-3

Cited by 6 publications

(3 citation statements)

References 21 publications

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“…Based on these building blocks we got target compounds vP-4539 and vP-4557 as previously reported [17][18][19] (Scheme 1, A). Using readily available endic-anhydride 3 we synthesized imides vP-4536 [20], vP-4521 [21], vP-4538 [22], vP-4540 [10] and amides vP-4511 [23], vP-4510 [29], vP-4520 of bicyclo[2.2.1]heptane(ene) series by applying common reactions (Scheme 1, B). Amidoacid vP-4543 was prepared [30] and used for bio-scree-ning for comparison with cage analog.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Palchykov¹,

Gaponov²,

Manko³

et al. 2022

Ukr.Biochem.J.

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Cage amides and imides bearing bicyclo[2.2.1]- and bicyclo[2.2.2]-subunits were synthesized and evaluated both for antimicrobial activity toward five key ESKAPE pathogenic bacteria: one Gram‐positive bacteria methicillin‐resistant Staphylococcus aureus (ATCC 43300), four Gram‐negative bacteria Escherichia coli (ATCC 25922), Klebsiella pneumoniae (ATCC 700603), Acinetobacter baumannii (ATCC 19606) and Pseudomonas aeruginosa (ATCC 27853) and for antifungal activity towards pathogenic fungal strains Candida albicans (ATCC 90028) and Cryptococcus neoformans var. Grubii (H99; ATCC 208821). Compound VP-4539 with bicyclo[2.2.2]octene motif demonstrated the highest cytotoxic activity towards C. neoformans, while human keratinocytes of HaCaT line, murine fibroblasts of Balb/c 3T3 line and mitogen-activated lymphocytes of peripheral human blood were found to be tolerant to its action. VP-4539 compound did not intercalate into salmon sperm DNA indicating that its cytotoxicity is not related to intercalation into nucleic acid. Keywords: antifungal, antimicrobial, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octene, cytotoxicity, DNA intercalation, human keratinocytes, lymphocytes, сage compounds

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Section: Resultsmentioning

confidence: 99%

“…All chemicals were of laboratory grade and used without further purification. The compounds were synthesized according to previously described synthetic procedures (vP-4539 [17][18][19], vP-4557 [17][18][19], vP-4536 [20], vP-4521 [21], vP-4511 [22], vP-4510 [23]). The full compound charac terizations are given in cited papers.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Palchykov¹,

Gaponov²,

Manko³

et al. 2022

Ukr.Biochem.J.

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“…Interestingly, to unequivocally establish all NMR assignments discussed above and to separate isomers 1 and 2, a simple conversion of the DA adducts to norbornyl amino acid esters (3 and 4) proved to be a successful strategy. [17][18] The reaction of the DA adducts mixture with L-alanine methyl ester yielded new derivatives that could be readily separated by chromatography on silica gel (Either column or automated Combiflash). These new compounds (3a, 3b, 4a and 4b), shown in Figure 12, exhibited interesting NMR spectra and can be used to introduce the students to another facet of diastereomer separation.…”

Section: (Furthermore Such Technique Could Be Applied To Other Ubiquitous Undergraduate Experiments Such As the Reduction Of Ketones And mentioning

confidence: 99%

The D iels‐ A lder Reaction with Maleic Anhydride*Present address, University of Southern California, Los Angeles, California.

Kloetzel

2011

Organic Reactions

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Analysis of a simple NMR spectrum is fairly easy and straight forward for undergraduate students but analyzing a fairly complex NMR can be very daunting and requires a methodical approach. This work uses the ubiquitous Diels-Alder reaction of methylcyclopentadiene and maleic anhydride to introduce students to an NMR spectrum that consist of inseparable mixtures of isomers and their analysis using advanced NMR spectroscopic techniques. This laboratory experiment further outlines the use of derivatization techniques for the separation of isomeric mixtures by preparing diastereomers and using NMR spectroscopy for their identification.

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Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

Bräse¹,

Meijere²

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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The carbopalladation of an alkene by an organylpalladium halide is the essential step in one of the major contemporary metal-catalyzed C-C coupling reactions. About 45 years ago, a Japanese and an American group almost simultaneously designed and executed palladium-mediated coupling reactions of aryl and alkenyl halides with alkenes [1]. In subsequent investigations, Richard Heck and his group developed this reaction into a catalytic transformation and started to demonstrate its usefulness as well as its rather broad scope. The real push to utilize this powerful C-C-bondforming process, however, started only around the mid-1980s, and by now, an impressive number of publications have established the meanwhile so-called Heck reaction [2] 1) as an indispensable method in Organic Synthesis [3][4][5][6][7]. The universal recognition of the importance of the Heck reaction and the Negishi as well as the Suzuki coupling eventually won the Nobel Prize for Richard Heck along with Ei-ichi Negishi and Akira Suzuki in 2010. The applications of the Heck reaction range from the preparation of -functionalized and unfunctionalized -hydrocarbons, novel polymers, and dyes to new advanced enantioselective syntheses of natural products and biologically active nonnatural compounds. The more or less simultaneous developments of mechanistically related variants, namely, the Kumada, Suzuki, Stille, Hiyama, and Negishi coupling reactions (Chapters 12, 2, 3, 4, and 15, respectively) of metallated alkenes and arenes with aryl and alkenyl halides or the metal-catalyzed formation and cycloisomerization of enynes have drawn profit from the improvement of and mechanistic insights into the Heck reaction. This, of course, applies vice versa as well. Using only a catalytic amount of a palladium(0) complex or a precursor to a palladium species, the Heck reaction can bring about unprecedented structural changes, particularly when conducted intramolecularly. The full potential of this palladium-catalyzed process is still being further explored as demonstrated by a total of over 7000 publications in the past 40 years by 1) The alkynylation of aryl and alkenyl halides, frequently also considered as Heck reactions, is described in Chapter 6.

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Synthesis of arylated norbornyl amino acid esters

Cited by 6 publications

References 21 publications

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

The D iels‐ A lder Reaction with Maleic Anhydride*Present address, University of Southern California, Los Angeles, California.

Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

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