Total Synthesis and Cytotoxicity Evaluation of an Oxazole Analogue of Tubulysin U

Shankar, Sreejith; Sani, Monica; Saunders, Fiona; Wallace, Heather M.; Zanda, Matteo

doi:10.1055/s-0030-1260806

Cited by 10 publications

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“…3 Owing to their remarkable interest and great potential as potent anticancer agents, se veral total syntheses of natural or modified tubulysins have been published. 4 Strucurally, tubulysins are linear tetrapeptides incorporating L-isoleucine and three unnatural amino acids. At the N-terminus, all the family members have N-methyl pipecolic acid ance for imparting the high potency typical of most cytotoxic natural tubulysins, such as A and D. Paolo Lazzari and co-workers at KemoTech (www.kemotech.it) have recently developed a scalable synthesis (up to one gram) of super-potent synthetic analogues of the natural tubulysins.…”

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“…3 Owing to their remarkable interest and great potential as potent anticancer agents, se veral total syntheses of natural or modified tubulysins have been published. 4 Strucurally Table) and (2) increased metabolic and chemical stability relative to the natural tubulysins, such as tubulysins A and D. In fact, KemoTech's proprietary tubulysins feature a highly stable alkylaryl, alkylcycloalkyl, alkylheteroaryl, etc. group R 2 replacing the labile and synthetically challenging alkoxycarbonylalkyl N-Tuv fragment which characterizes the natural tubulysins.…”

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Which aspects of your academic work do you like the most? The last two weeks were quite mixed and intense for me; normally I do not have much teaching (don't tell it to my College though...) but in the last few days I had to mark a few exams and I dealt with some other teaching-related activity too. Then, I organized a one-day workshop with ca. 50 attendees. I have also been finalizing a grant application, drafting a couple of manuscripts, evaluated several grant applications and a couple of manuscripts, dealt with the usual supervision of my postgraduate students and postdocs. Then, I did quite a lot of 'administration' work connected with the fact that I am directing two research centers of my university. And obviously I took care of SYN-FORM. Plus some other miscellaneous stuff. Luckily, I did not have to travel. But, unfortunately, I had very little time for keeping myself up-to-date with the literature, which is something that really annoys me. That's because studying the literature and designing new experiments and projects is by far my favorite activity, I really love browsing journals online and getting inspiration and ideas for new research endeavors. I guess many of you will agree that this is what really makes our work special, together with the excitement of seeing our research plans materialized into exciting experimental results, expected or not (which sometimes is even better!). And I suspect this sentiment is also shared by the researchers whose work is featured in this new issue of SYN-FORM, which includes the following SYNSTORIES: the Pd-catalyzed C-H γ-arylation of α-amino acids reported by J. C. Carretero (Spain); a novel stereoselective approach to all-carbon quaternary stereocenters catalyzed by peptides, discovered by K. Kudo (Japan); a novel synthetic approach to βand γ-hydroxy sulfides developed by J. Leazer (USA); the FEATURED SYNSTORY on the highly potent toxic payloads for targeted chemotherapy developed by P. Lazzari and his company (Italy). Enjoy your reading! Editor of SYNFORM SYNFORM A28 IN THIS ISSUE SYNSTORIES Palladium-Catalyzed N-(2-Pyridyl)sulfonyl-Directed C(sp 3)-H γ-Arylation of Amino Acid Derivatives. .

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Yo ur op ini on ab ou t SY NF OR M is we lco me , ple as e co rre sp on d if yo u lik e: ma rk et ing @t hie me -c he mi str y.c om Dear readers,Which aspects of your academic work do you like the most? The last two weeks were quite mixed and intense for me; normally I do not have much teaching (don't tell it to my College though...) but in the last few days I had to mark a few exams and I dealt with some other teaching-related activity too. Then, I organized a one-day workshop with ca. 50 attendees. I have also been finalizing a grant application, drafting a couple of manuscripts, evaluated several grant applications and a couple of manuscripts, dealt with the usual supervision of my postgraduate students and postdocs. Then, I did quite a lot of 'administration' work connected with the fact that I am directing two research centers of my university. And obviously I took care of SYN-FORM. Plus some other miscellaneous stuff. Luckily, I did not have to travel. But, unfortunately, I had very little time for keeping myself up-to-date with the literature, which is something that really annoys me. That's because studying the literature and designing new experiments and projects is by far my favorite activity, I really love browsing journals online and getting inspiration and ideas for new research endeavors. I guess many of you will agree that this is what really makes our work special, together with the excitement of seeing our research plans materialized into exciting experimental results, expected or not (which sometimes is even better!). And I suspect this sentiment is also shared by the researchers whose work is featured in this new issue of SYN-FORM, which includes the following SYNSTORIES: the Pd-catalyzed C-H γ-arylation of α-amino acids reported by J. C. Carretero (Spain); a novel stereoselective approach to all-carbon quaternary stereocenters catalyzed by peptides, discovered by K. Kudo (Japan); a novel synthetic approach to βand γ-hydroxy sulfides developed by J. Leazer (USA); the FEATURED SYNSTORY on the highly potent toxic payloads for targeted chemotherapy developed by P. Lazzari and his company (Italy). Enjoy your reading! Editor of SYNFORM SYNFORM A28 IN THIS ISSUE SYNSTORIES Palladium-Catalyzed N-(2-Pyridyl)sulfonyl-Directed C(sp 3 ) -H γ-Arylation of Amino Acid Derivatives . .

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Total Synthesis and Cytotoxicity Evaluation of an Oxazole Analogue of Tubulysin U

Cited by 10 publications

References 8 publications

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Synform Issue 2013/3

Synform Issue 2013/3

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