FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2317167430> ?p ?o ?g. }

• W2317167430 endingPage "1171" @default.
• W2317167430 startingPage "1159" @default.
• W2317167430 abstract "Natural products chemistry has historically been the prime arena for the discovery of new chemical transformations and the fountain of insights into key biological processes. It remains a fervent incubator of progress in the fields of chemistry and biology and an exchange mediating the flow of ideas between these allied fields of science. It is with this ethos that our group has taken an interest in and pursued the synthesis of a complex family of natural products termed the dimeric epipolythiodiketopiperazine (ETP) alkaloids. We present here an Account of the highly complex target molecules to which we pegged our ambitions, our systematic and relentless efforts toward those goals, the chemistry we developed in their pursuit, and the insight we have gained for their translational potential as potent anticancer molecules. The dimeric ETP alkaloids are fungal metabolites that feature a highly complex molecular architecture comprising a densely functionalized core structure with many stereogenic centers, six of which are fully substituted, and a pair of vicinal quaternary carbon stereocenters, decorated on polycyclic architectures in addition to the unique ETP motif that has been recognized as acid-, base-, and redox-sensitive. A cyclo-dipeptide consisting of an essential tryptophan residue and a highly variable ancillary amino acid lies at the core of these structures; investigation of the transformations that take this simplistic core to the complex alkaloids lies at the heart of our research program. The dimeric epidithiodiketopiperazine alkaloids have largely resisted synthesis on account of their complexity since the 1970s when the founding members of this class, chaetocin A ( Hauser , D. et al. Helv. Chim. Acta 1970 , 53 , 1061 ) and verticillin A ( Katagiri , K. et al. J. Antibiot. 1970 , 23 , 420 ), were first isolated. This was despite their potent cytotoxic and bacteriostatic activities, which were well appreciated at the time of their discovery. In the past decade, an increasing number of studies have uncovered powerful new biological processes that these molecules can uniquely effect, such as the inhibition of histone methyltransferases by chaetocin A ( Greiner , D. et al. Nat. Chem. Biol. 2005 , 1 , 143 ). In fact, the complete collection of hexahydropyrroloindoline alkaloids features a diverse range of potent biological properties including cytotoxic, antitumor, antileukemic, antiviral, antibiotic, and antinematodal activities ( Jiang , C.-S. ; Guo , Y.-W. Mini-Rev. Med. Chem. 2011 , 11 , 728 ). This mélange of activities is reflective of their structural diversity. Under the precepts of retrobiosynthetic analysis, we have accomplished the syntheses of more than a dozen natural products, including members of the bionectin, calycanthaceous, chaetocin, gliocladin, naseseazine, and verticillin alkaloids. More importantly, these molecules have acted as venerable venues for the development of new strategies to address structural challenges including, but not limited to, C3-C3' vicinal quaternary centers, heterodimeric linkages, C3-Csp(2) linkages, diketopiperazine oxidation, stereoselective thiolation, homologue-specific polysulfidation, and C12-hydroxyl incorporation. Synthesis of these natural products has resulted in the structural confirmation, and sometimes revision such as the case of (+)-naseseazines A and B, as well as access to many plausible biogenetically relevant intermediates and new synthetic ETP derivatives. Furthermore, our studies have paved the way for the formulation of a comprehensive SAR profile and the identification of lead compounds with in vitro subnanomolar IC50's against a broad range of cancer types." @default.
• W2317167430 created "2016-06-24" @default.
• W2317167430 creator A5057797551 @default.
• W2317167430 creator A5081366480 @default.
• W2317167430 date "2015-04-06" @default.
• W2317167430 modified "2023-10-10" @default.
• W2317167430 title "Biogenetically-Inspired Total Synthesis of Epidithiodiketopiperazines and Related Alkaloids" @default.
• W2317167430 cites W1539307520 @default.
• W2317167430 cites W1943174022 @default.
• W2317167430 cites W1964098571 @default.
• W2317167430 cites W1964301999 @default.
• W2317167430 cites W1971126857 @default.
• W2317167430 cites W1985593906 @default.
• W2317167430 cites W1987174164 @default.
• W2317167430 cites W1997679625 @default.
• W2317167430 cites W1998537255 @default.
• W2317167430 cites W1999506476 @default.
• W2317167430 cites W2010429928 @default.
• W2317167430 cites W2027057367 @default.
• W2317167430 cites W2028882076 @default.
• W2317167430 cites W2035710040 @default.
• W2317167430 cites W2036920720 @default.
• W2317167430 cites W2043998094 @default.
• W2317167430 cites W2049070043 @default.
• W2317167430 cites W2064286197 @default.
• W2317167430 cites W2064337480 @default.
• W2317167430 cites W2068792036 @default.
• W2317167430 cites W2078030302 @default.
• W2317167430 cites W2081905442 @default.
• W2317167430 cites W2084591130 @default.
• W2317167430 cites W2097125303 @default.
• W2317167430 cites W2105804977 @default.
• W2317167430 cites W2106541335 @default.
• W2317167430 cites W2109773568 @default.
• W2317167430 cites W2123117845 @default.
• W2317167430 cites W2123624477 @default.
• W2317167430 cites W2126347045 @default.
• W2317167430 cites W2132095296 @default.
• W2317167430 cites W2155215477 @default.
• W2317167430 cites W2159221213 @default.
• W2317167430 cites W2162490925 @default.
• W2317167430 cites W2167116907 @default.
• W2317167430 cites W2169883424 @default.
• W2317167430 cites W2479557569 @default.
• W2317167430 cites W2952634576 @default.
• W2317167430 cites W2953122576 @default.
• W2317167430 cites W4244014648 @default.
• W2317167430 cites W4375916329 @default.
• W2317167430 doi "https://doi.org/10.1021/ar500454v" @default.
• W2317167430 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4408872" @default.
• W2317167430 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25843276" @default.
• W2317167430 hasPublicationYear "2015" @default.
• W2317167430 type Work @default.
• W2317167430 sameAs 2317167430 @default.
• W2317167430 citedByCount "152" @default.
• W2317167430 countsByYear W23171674302015 @default.
• W2317167430 countsByYear W23171674302016 @default.
• W2317167430 countsByYear W23171674302017 @default.
• W2317167430 countsByYear W23171674302018 @default.
• W2317167430 countsByYear W23171674302019 @default.
• W2317167430 countsByYear W23171674302020 @default.
• W2317167430 countsByYear W23171674302021 @default.
• W2317167430 countsByYear W23171674302022 @default.
• W2317167430 countsByYear W23171674302023 @default.
• W2317167430 crossrefType "journal-article" @default.
• W2317167430 hasAuthorship W2317167430A5057797551 @default.
• W2317167430 hasAuthorship W2317167430A5081366480 @default.
• W2317167430 hasBestOaLocation W23171674301 @default.
• W2317167430 hasConcept C134195300 @default.
• W2317167430 hasConcept C146686406 @default.
• W2317167430 hasConcept C161790260 @default.
• W2317167430 hasConcept C178790620 @default.
• W2317167430 hasConcept C185592680 @default.
• W2317167430 hasConcept C21951064 @default.
• W2317167430 hasConcept C71240020 @default.
• W2317167430 hasConceptScore W2317167430C134195300 @default.
• W2317167430 hasConceptScore W2317167430C146686406 @default.
• W2317167430 hasConceptScore W2317167430C161790260 @default.
• W2317167430 hasConceptScore W2317167430C178790620 @default.
• W2317167430 hasConceptScore W2317167430C185592680 @default.
• W2317167430 hasConceptScore W2317167430C21951064 @default.
• W2317167430 hasConceptScore W2317167430C71240020 @default.
• W2317167430 hasFunder F4320307105 @default.
• W2317167430 hasFunder F4320337354 @default.
• W2317167430 hasIssue "4" @default.
• W2317167430 hasLocation W23171674301 @default.
• W2317167430 hasLocation W23171674302 @default.
• W2317167430 hasLocation W23171674303 @default.
• W2317167430 hasLocation W23171674304 @default.
• W2317167430 hasLocation W23171674305 @default.
• W2317167430 hasOpenAccess W2317167430 @default.
• W2317167430 hasPrimaryLocation W23171674301 @default.
• W2317167430 hasRelatedWork W1552623351 @default.
• W2317167430 hasRelatedWork W1967770564 @default.
• W2317167430 hasRelatedWork W2000102181 @default.
• W2317167430 hasRelatedWork W2013211788 @default.
• W2317167430 hasRelatedWork W2052856723 @default.
• W2317167430 hasRelatedWork W2122645677 @default.

• next