lactams

Summary

Summary: Cyclic AMIDES formed from aminocarboxylic acids by the elimination of water. Lactims are the enol forms of lactams.

Top Publications

  1. Enz A, Feuerbach D, Frederiksen M, Gentsch C, Hurth K, Muller W, et al. Gamma-lactams--a novel scaffold for highly potent and selective alpha 7 nicotinic acetylcholine receptor agonists. Bioorg Med Chem Lett. 2009;19:1287-91 pubmed publisher
    ..The cis gamma-lactam scaffold has been optimized to reveal highly potent and selective alpha7 nAChR agonists with in vitro activity and selectivity and with good brain penetration in mice...
  2. Tan D, Younai A, Pattawong O, Fettinger J, Cheong P, Shaw J. Stereoselective synthesis of ?-lactams from imines and cyanosuccinic anhydrides. Org Lett. 2013;15:5126-9 pubmed publisher
    ..The synthesis of highly substituted ?-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and ..
  3. Chung C, Hsu C, Lin J, Kuo Y, Chiang W, Lin Y. Antiproliferative lactams and spiroenone from adlay bran in human breast cancer cell lines. J Agric Food Chem. 2011;59:1185-94 pubmed publisher
    Two new lactams, coixspirolactam D (1) and coixspirolactam E (2), and a new spiroenone, coixspiroenone (3), together with seven known compounds, coixspirolactam A (4), coixspirolactam B (5), coixspirolactam C (6), coixlactam (7), coixol (..
  4. Gaudelli N, Townsend C. Stereocontrolled syntheses of peptide thioesters containing modified seryl residues as probes of antibiotic biosynthesis. J Org Chem. 2013;78:6412-26 pubmed publisher
  5. Charusanti P, Fong N, Nagarajan H, Pereira A, Li H, Abate E, et al. Exploiting adaptive laboratory evolution of Streptomyces clavuligerus for antibiotic discovery and overproduction. PLoS ONE. 2012;7:e33727 pubmed publisher
    ..These results demonstrate that competition-based adaptive laboratory evolution can constitute a platform to create mutants that overproduce known antibiotics and possibly to discover new compounds as well...
  6. Nárdiz N, Santamarta I, Lorenzana L, Martin J, Liras P. A rhodanese-like protein is highly overrepresented in the mutant S. clavuligerus oppA2::aph: effect on holomycin and other secondary metabolites production. Microb Biotechnol. 2011;4:216-25 pubmed publisher
    ..clavuligerus...
  7. Wardrop D, Bowen E, Forslund R, Sussman A, Weerasekera S. Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams. J Am Chem Soc. 2010;132:1188-9 pubmed publisher
    The development of a versatile method for the preparation of five- to eight-membered hydroxy lactams that involves the iodine(III)-mediated oxamidation of unsaturated O-alkyl hydroxamates is described...
  8. Zhao X, DiRocco D, Rovis T. N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-?-lactams. J Am Chem Soc. 2011;133:12466-9 pubmed publisher
    An efficient enantioselective approach to form trans-?-lactams in up to 99% yield, 93% ee, and >20/1 dr using unactivated imines has been developed...
  9. Huang Y, Cui J, Chen S, Gan C, Zhou A. Synthesis and antiproliferative activity of some steroidal lactams. Steroids. 2011;76:1346-50 pubmed publisher
    ..and the cytotoxic activity against MGC 7901 and SMMC 7404 cells was not significantly different between 4-N-lactams and 3-N-lactams when its 6-substituted group was a carbonyl or a hydroximino, but all 3-N-lactams showed a higher ..

More Information

Publications71

  1. Lim S, Qin X, Susser S, Nicholas J, Lange C, Herrmann E, et al. Virologic escape during danoprevir (ITMN-191/RG7227) monotherapy is hepatitis C virus subtype dependent and associated with R155K substitution. Antimicrob Agents Chemother. 2012;56:271-9 pubmed publisher
    ..These data indicate the ascendant importance of R155K for viral escape during danoprevir treatment and may have implications for the clinical use of this agent...
  2. Wietz M, Mansson M, Gotfredsen C, Larsen T, Gram L. Antibacterial compounds from marine Vibrionaceae isolated on a global expedition. Mar Drugs. 2010;8:2946-60 pubmed publisher
    ..halotolerans). Despite the isolation of already known antibiotics, our findings show that marine Vibrionaceae are a resource of antibacterial compounds and may have potential for future natural product discovery...
  3. Li B, Forseth R, Bowers A, Schroeder F, Walsh C. A backup plan for self-protection: S-methylation of holomycin biosynthetic intermediates in Streptomyces clavuligerus. Chembiochem. 2012;13:2521-6 pubmed publisher
    ..Furthermore, bioassays suggest that modification of the enethiol warhead by S-alkylation provides a host strategy for detoxification, one that is shared amongst multiple species producing such bioactive disulfide natural products...
  4. Gane E, Roberts S, Stedman C, Angus P, Ritchie B, Elston R, et al. Oral combination therapy with a nucleoside polymerase inhibitor (RG7128) and danoprevir for chronic hepatitis C genotype 1 infection (INFORM-1): a randomised, double-blind, placebo-controlled, dose-escalation trial. Lancet. 2010;376:1467-75 pubmed publisher
  5. Qin Z, Baker A, Raab A, Huang S, Wang T, Yu Y, et al. The fish pathogen Yersinia ruckeri produces holomycin and uses an RNA methyltransferase for self-resistance. J Biol Chem. 2013;288:14688-97 pubmed publisher
    ..Taken together, our results strongly suggest that this putative RNA methyltransferase Hom12 is the self-resistance protein that methylates the RNA of Y. ruckeri to reduce the cytotoxic effect of holomycin during holomycin production...
  6. Li B, Walsh C. Identification of the gene cluster for the dithiolopyrrolone antibiotic holomycin in Streptomyces clavuligerus. Proc Natl Acad Sci U S A. 2010;107:19731-5 pubmed publisher
    ..Purified ORF3483 shows acyltransferase activity, converting holothin to holomycin and longer acylated homologs as the last step in antibiotic assembly...
  7. Forestier N, Larrey D, Guyader D, Marcellin P, Rouzier R, Patat A, et al. Treatment of chronic hepatitis C patients with the NS3/4A protease inhibitor danoprevir (ITMN-191/RG7227) leads to robust reductions in viral RNA: a phase 1b multiple ascending dose study. J Hepatol. 2011;54:1130-6 pubmed publisher
    ..The present study assessed the safety, pharmacokinetics, and antiviral activity of danoprevir in a randomized, placebo-controlled, 14-day multiple ascending dose study in patients with chronic HCV genotype 1 infection...
  8. Robles Reglero V, Santamarta I, Alvarez Alvarez R, Martin J, Liras P. Transcriptional analysis and proteomics of the holomycin gene cluster in overproducer mutants of Streptomyces clavuligerus. J Biotechnol. 2013;163:69-76 pubmed publisher
    ..coelicolor M1154 strain, suggesting that heterologous expression in S. coelicolor might be toxic due to the lack of an holomycin resistance gene in this host strain...
  9. Nair L, Sannigrahi M, Bogen S, Pinto P, Chen K, Prongay A, et al. P4 capped amides and lactams as HCV NS3 protease inhibitors with improved potency and DMPK profile. Bioorg Med Chem Lett. 2010;20:567-70 pubmed publisher
    SAR studies on the extension of P3 unit of Boceprevir (1, SCH 503034) with amides and lactams and their synthesis is described...
  10. Bae A, Sun S, Qi X, Chen X, Ku K, Worth A, et al. Susceptibility of treatment-naive hepatitis C virus (HCV) clinical isolates to HCV protease inhibitors. Antimicrob Agents Chemother. 2010;54:5288-97 pubmed publisher
    ..Our results suggest that the natural variation in baseline susceptibility may contribute to different degrees of antiviral response among patients in vivo, particularly at lower doses...
  11. Edler M, Yang G, Katherine Jung M, Bai R, Bornmann W, Hamel E. Demonstration of microtubule-like structures formed with (-)-rhazinilam from purified tubulin outside of cells and a simple tubulin-based assay for evaluation of analog activity. Arch Biochem Biophys. 2009;487:98-104 pubmed publisher
    ..This mixed polymer slowly disassembled at 0 degrees C, but there was no apparent difference in the lability of the microtubules versus the spirals...
  12. Davidsen J, Townsend C. In vivo characterization of nonribosomal peptide synthetases NocA and NocB in the biosynthesis of nocardicin A. Chem Biol. 2012;19:297-306 pubmed publisher
    ..Conversely, production of nocardicin A was not affected by mutation of the NocB histidine motif or the R828G mutation in NocA...
  13. Balansa W, Islam R, Fontaine F, Piggott A, Zhang H, Xiao X, et al. Sesterterpene glycinyl-lactams: a new class of glycine receptor modulator from Australian marine sponges of the genus Psammocinia. Org Biomol Chem. 2013;11:4695-701 pubmed publisher
    ..The discovery and characterization of sesterterpenes 1-8, and in particular the glycinyl-lactams 3 and 6, provide valuable new insights into GlyR pharmacology...
  14. Szostak M, Yao L, Day V, Powell D, AUBE J. Structural characterization of N-protonated amides: regioselective N-activation of medium-bridged twisted lactams. J Am Chem Soc. 2010;132:8836-7 pubmed publisher
    The straightforward protonation of lactams by treatment with acid and the full structural characterization of three resulting N-protonated lactams are disclosed...
  15. Fukuda D, Haines A, Song Z, Murphy A, Hothersall J, Stephens E, et al. A natural plasmid uniquely encodes two biosynthetic pathways creating a potent anti-MRSA antibiotic. PLoS ONE. 2011;6:e18031 pubmed publisher
  16. Li B, Walsh C. Streptomyces clavuligerus HlmI is an intramolecular disulfide-forming dithiol oxidase in holomycin biosynthesis. Biochemistry. 2011;50:4615-22 pubmed publisher
  17. Tan D, Martin K, Fettinger J, Shaw J. Ammonia synthons for the multicomponent assembly of complex gamma-lactams. Proc Natl Acad Sci U S A. 2011;108:6781-6 pubmed publisher
    The synthesis of ?-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported...
  18. Yin H, Xiang S, Zheng J, Fan K, Yu T, Yang X, et al. Induction of holomycin production and complex metabolic changes by the argR mutation in Streptomyces clavuligerus NP1. Appl Environ Microbiol. 2012;78:3431-41 pubmed publisher
    ..clavuligerus...
  19. Forestier N, Larrey D, Marcellin P, Guyader D, Patat A, Rouzier R, et al. Antiviral activity of danoprevir (ITMN-191/RG7227) in combination with pegylated interferon ?-2a and ribavirin in patients with hepatitis C. J Infect Dis. 2011;204:601-8 pubmed publisher
    ..Current therapy options for patients with chronic hepatitis C virus (HCV) infection genotype 1 are effective in <50%. Danoprevir (ITMN-191/RG7227) is a potent, selective, and orally active inhibitor of the HCV NS3/4A serine protease...
  20. Ciesek S, von Hahn T, Manns M. Second-wave protease inhibitors: choosing an heir. Clin Liver Dis. 2011;15:597-609 pubmed publisher
    ..This article gives an overview of the compounds that will soon be available...
  21. Gottwein J, Scheel T, Jensen T, Ghanem L, Bukh J. Differential efficacy of protease inhibitors against HCV genotypes 2a, 3a, 5a, and 6a NS3/4A protease recombinant viruses. Gastroenterology. 2011;141:1067-79 pubmed publisher
    ..Because there are limited or no data on efficacy against HCV genotypes 2-7, we aimed at developing recombinant infectious cell culture systems expressing genotype-specific nonstructural (NS) protein 3 protease (NS3P)...
  22. Davidsen J, Bartley D, Townsend C. Non-ribosomal propeptide precursor in nocardicin A biosynthesis predicted from adenylation domain specificity dependent on the MbtH family protein NocI. J Am Chem Soc. 2013;135:1749-59 pubmed publisher
    ..uniformis...
  23. Blunt J, Copp B, Keyzers R, Munro M, Prinsep M. Marine natural products. Nat Prod Rep. 2013;30:237-323 pubmed publisher
    ..Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included...
  24. Dhingra N, Bhardwaj T, Mehta N, Mukhopadhyay T, Kumar A, Kumar M. Synthesis, antiproliferative, acute toxicity and assessment of antiandrogenic activities of some newly synthesized steroidal lactams. Eur J Med Chem. 2010;45:2229-36 pubmed publisher
    ..Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data and pharmacological screening for the synthesized compounds were reported...
  25. Babu B, Endo Y, Bäckvall J. Biomimetic aerobic oxidation of amino alcohols to lactams. Chemistry. 2012;18:11524-7 pubmed publisher
    The right path: N-protected amino alcohols undergo aerobic and biomimetic oxidation to the corresponding lactams in the presence of a ruthenium catalyst and a combination of electron-transfer mediators under air (see scheme)...
  26. Albrecht A, Morana F, Fraile A, Jørgensen K. Organophosphorus reagents in organocatalysis: synthesis of optically active ?-methylene-?-lactones and ?-lactams. Chemistry. 2012;18:10348-54 pubmed publisher
    ..new asymmetric, catalytic strategies for the synthesis of biologically important ?-methylene-?-lactones and ?-lactams. The elaborated protocols utilize iminium-ion-mediated Michael addition of trimethyl phosphonoacetate to ?,?-..
  27. Gane E, Rouzier R, Stedman C, Wiercinska Drapalo A, Horban A, Chang L, et al. Antiviral activity, safety, and pharmacokinetics of danoprevir/ritonavir plus PEG-IFN ?-2a/RBV in hepatitis C patients. J Hepatol. 2011;55:972-9 pubmed publisher
  28. Tang G, Cheng Y, Shen B. Leinamycin biosynthesis revealing unprecedented architectural complexity for a hybrid polyketide synthase and nonribosomal peptide synthetase. Chem Biol. 2004;11:33-45 pubmed
    ..These studies unveil an unprecedented architectural complexity for the LNM hybrid NRPS-PKS megasynthetase and set the stage to investigate the molecular basis for LNM biosynthesis. ..
  29. Lillelund V, Liu H, Liang X, Søhoel H, Bols M. Isofagomine lactams, synthesis and enzyme inhibition. Org Biomol Chem. 2003;1:282-7 pubmed
    The synthesis of isofagomine lactams (2-oxoisofagomines) corresponding to the biologically important hexoses is presented...
  30. Kelly W, Townsend C. Role of the cytochrome P450 NocL in nocardicin A biosynthesis. J Am Chem Soc. 2002;124:8186-7 pubmed
    ..This is the first gene from this pathway to be expressed and its function established, and it is the first example of oxime formation from a primary amine in bacteria unambiguously linked to a cytochrome P450. ..
  31. Kelly W, Townsend C. Mutational analysis and characterization of nocardicin C-9' epimerase. J Biol Chem. 2004;279:38220-7 pubmed
  32. Couture A, Deniau E, Grandclaudon P, Rybalko Rosen H, Leonce S, Pfeiffer B, et al. Synthesis and biological evaluation of aristolactams. Bioorg Med Chem Lett. 2002;12:3557-9 pubmed
    ..Modulations were carried out on the phenanthrene nucleus and the lactam moiety as well. N-(N-dialkylaminoalkyl) derivatives exhibited interesting cytotoxic activity against the L1210 leukemia cell line...
  33. Jakubec P, Helliwell M, Dixon D. Cyclic imine nitro-Mannich/lactamization cascades: a direct stereoselective synthesis of multicyclic piperidinone derivatives. Org Lett. 2008;10:4267-70 pubmed publisher
    ..The reaction is broad in scope and stereoselective and may be coupled to an enantioselective nitroolefin Michael addition reaction as part of a highly enantio- and diastereoselective multicomponent process. ..
  34. Macdonald S, Dowle M, Harrison L, Clarke G, Inglis G, Johnson M, et al. Discovery of further pyrrolidine trans-lactams as inhibitors of human neutrophil elastase (HNE) with potential as development candidates and the crystal structure of HNE complexed with an inhibitor (GW475151). J Med Chem. 2002;45:3878-90 pubmed
    ..GW311616A, 1, a derivative of pyrrolidine trans-lactams, has previously been described as a potent, orally active inhibitor of human neutrophil elastase (HNE) for the ..
  35. Wei J, Shaw J. Diastereoselective synthesis of gamma-lactams by a one-pot, four-component reaction. Org Lett. 2007;9:4077-80 pubmed
    ..amines, maleic anhydrides, aldehydes, and thiols has been discovered to form tetra- and pentasubstituted gamma-lactams with high diastereoselectivity...
  36. Moscatelli A, Ciampolini F, Rodighiero S, Onelli E, Cresti M, Santo N, et al. Distinct endocytic pathways identified in tobacco pollen tubes using charged nanogold. J Cell Sci. 2007;120:3804-19 pubmed
    ..However, intact positively charged-nanogold transport to vacuoles supports the idea that an endocytic pathway that does not require clathrin is also present in pollen tubes. ..
  37. Newhouse B, Allen S, Fauber B, Anderson A, Eary C, Hansen J, et al. Racemic and chiral lactams as potent, selective and functionally active CCR4 antagonists. Bioorg Med Chem Lett. 2004;14:5537-42 pubmed
    A series of racemic and chiral, nonracemic lactams that display high binding affinities, functional chemotaxis antagonism, and selectivity toward CCR4 are described...
  38. Nagarajan M, Xiao X, Antony S, Kohlhagen G, Pommier Y, Cushman M. Design, synthesis, and biological evaluation of indenoisoquinoline topoisomerase I inhibitors featuring polyamine side chains on the lactam nitrogen. J Med Chem. 2003;46:5712-24 pubmed
    ..07 microM in the NIH human cancer cell culture screen, and topoisomerase I inhibitory activity comparable to that of camptothecin...
  39. Chen S, Borowiak M, Fox J, Maehr R, Osafune K, Davidow L, et al. A small molecule that directs differentiation of human ESCs into the pancreatic lineage. Nat Chem Biol. 2009;5:258-65 pubmed publisher
    ..This study describes a chemical screening platform to investigate human ESC differentiation and demonstrates the generation of a cell population that is a key milepost on the path to making beta cells...
  40. Gomez C, Bai L, Zhang J, Nikolovska Coleska Z, Chen J, Yi H, et al. Design, synthesis, and evaluation of peptidomimetics containing Freidinger lactams as STAT3 inhibitors. Bioorg Med Chem Lett. 2009;19:1733-6 pubmed publisher
    ..In this letter, we describe the design, synthesis, and evaluation of peptidomimetics containing Freidinger lactams as novel STAT3 inhibitors...
  41. de la Fuente A, Lorenzana L, Martin J, Liras P. Mutants of Streptomyces clavuligerus with disruptions in different genes for clavulanic acid biosynthesis produce large amounts of holomycin: possible cross-regulation of two unrelated secondary metabolic pathways. J Bacteriol. 2002;184:6559-65 pubmed
    ..This enzyme forms holomycin from holothin by using acetyl coenzyme A as an acetyl group donor. The holomycin synthase activities in the different clavulanic acid mutants correlate well with their production of holomycin...
  42. Hamilton Miller J. Chemical and microbiologic aspects of penems, a distinct class of beta-lactams: focus on faropenem. Pharmacotherapy. 2003;23:1497-507 pubmed
    ..Penems form a discrete class of beta-lactams that comprises structural hybrids of penicillins (penams) and cephalosporins (cephems)...
  43. Kumar V, Poonam -, Prasad A, Parmar V. Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities. Nat Prod Rep. 2003;20:565-83 pubmed
    ..In this report, these three important classes of natural products are reviewed and classified on the basis of their oxygenation pattern. In addition the biological activities of these compounds and their general chemistry are discussed...
  44. Lemaire S, Van Bambeke F, Mingeot Leclercq M, Tulkens P. Activity of three {beta}-lactams (ertapenem, meropenem and ampicillin) against intraphagocytic Listeria monocytogenes and Staphylococcus aureus. J Antimicrob Chemother. 2005;55:897-904 pubmed
    Assessment of the activity of three beta-lactams [ertapenem (a carbapenem with a prolonged half-life), meropenem and ampicillin] against intraphagocytic Listeria monocytogenes and Staphylococcus aureus.
  45. Kutuk O, Pedrech A, Harrison P, Basaga H. Pramanicin induces apoptosis in Jurkat leukemia cells: a role for JNK, p38 and caspase activation. Apoptosis. 2005;10:597-609 pubmed
    ..These results suggest pramanicin as a potential apoptosis-inducing small molecule, which acts through a well-defined JNK- and p38-dependent apoptosis signalling pathway in Jurkat T leukemia cells...
  46. Davidsen J, Townsend C. Identification and characterization of NocR as a positive transcriptional regulator of the beta-lactam nocardicin A in Nocardia uniformis. J Bacteriol. 2009;191:1066-77 pubmed publisher
    ..These experiments establish NocR as a positive transcriptional regulator of the nocardicin A biosynthetic pathway, coordinating the initial steps of nocardicin A biosynthesis to the production of its pHPG precursor...
  47. Hou Y, Li F, Wang S, Qin S, Wang Q. Intergeneric conjugation in holomycin-producing marine Streptomyces sp. strain M095. Microbiol Res. 2008;163:96-104 pubmed
  48. Borthwick A, Exall A, Haley T, Jackson D, Mason A, Weingarten G. Pyrrolidine-5,5-trans-lactams as novel mechanism-based inhibitors of human cytomegalovirus protease. Part 3: potency and plasma stability. Bioorg Med Chem Lett. 2002;12:1719-22 pubmed
  49. Hughes G, Kimura M, Buchwald S. Catalytic enantioselective conjugate reduction of lactones and lactams. J Am Chem Soc. 2003;125:11253-8 pubmed
    ..acceleration of the enantioselective copper-catalyzed conjugate reduction of alpha,beta-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives...
  50. Kwan C, Zhang W, Miller J, Harrison P, Kassan S, Liscombe D. The epoxy group of pramanicin is required for the optimal endothelium-dependent relaxation of rat aorta. J Pharmacol Sci. 2003;92:203-8 pubmed
    ..The potent, selective, and irreversible inhibitory effect of PMC on the endothelial function points to its potential development into an anti-angiogenic drug...
  51. Scanlan E, Slawin A, Walton J. Preparation of beta- and gamma-lactams from carbamoyl radicals derived from oxime oxalate amides. Org Biomol Chem. 2004;2:716-24 pubmed
    ..GC-MS evidence indicated that this radical cyclised to afford some of the corresponding penicillin derivative..
  52. Han C, Rangarajan S, Voukides A, Beeler A, Johnson R, Porco J. Reaction discovery employing macrocycles: transannular cyclizations of macrocyclic bis-lactams. Org Lett. 2009;11:413-6 pubmed publisher
    Macrocyclic bis-lactams have been synthesized by cyclodimerization of homoallylic amino esters employing a Zr(IV)-catalyzed ester-amide exchange protocol...
  53. Kwan C, Harrison P, Duspara P, Daniel E. Vasorelaxant effects of pramanicin, an anti-fungal agent: selective action on endothelial cells. Jpn J Pharmacol. 2001;85:234-40 pubmed
    ..This is followed by a cytotoxic effect on vascular endothelial cells, eventually resulting in the loss of vasorelaxant function...
  54. Krstić N, Bjelaković M, Zizak Z, Pavlović M, Juranic Z, Pavlović V. Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities. Steroids. 2007;72:406-14 pubmed
    ..The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined...
  55. Luo T, Fredericksen B, Hasumi K, Endo A, Garcia J. Human immunodeficiency virus type 1 Nef-induced CD4 cell surface downregulation is inhibited by ikarugamycin. J Virol. 2001;75:2488-92 pubmed
    ..In addition, we demonstrate that IKA is also capable of efficiently blocking CD4 down-modulation in response to phorbol myristate acetate. Our data suggest that IKA may be an efficient and useful inhibitor of CCP-dependent endocytosis...
  56. Kwan C, Harrison P, Kwan T. Pramanicin, an antifungal agent, raises cytosolic Ca2+ and causes cell death in vascular endothelial cells. Vascul Pharmacol. 2003;40:35-42 pubmed
  57. Slater M, Amphlett E, Andrews D, Bamborough P, Carey S, Johnson M, et al. Pyrrolidine-5,5-trans-lactams. 4. Incorporation of a P3/P4 urea leads to potent intracellular inhibitors of hepatitis C virus NS3/4A protease. Org Lett. 2003;5:4627-30 pubmed
    ..Compound 7b demonstrated a 100 nM IC(50) in the replicon cell-based surrogate HCV assay...
  58. Amat M, Lozano O, Escolano C, Molins E, Bosch J. Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams. J Org Chem. 2007;72:4431-9 pubmed
    The stereochemical outcome of the enolate dialkylation of simple phenylglycinol-derived oxazolopiperidone lactams is studied...
  59. Masse C, Ng P, Fukase Y, Sánchez Roselló M, Shaw J. Divergent structural complexity from a linear reaction sequence: synthesis of fused and spirobicyclic gamma-lactams from common synthetic precursors. J Comb Chem. 2006;8:293-6 pubmed
  60. Nagarajan M, Morrell A, Ioanoviciu A, Antony S, Kohlhagen G, Agama K, et al. Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles. J Med Chem. 2006;49:6283-9 pubmed
  61. Gunsior M, Breazeale S, Lind A, Ravel J, Janc J, Townsend C. The biosynthetic gene cluster for a monocyclic beta-lactam antibiotic, nocardicin A. Chem Biol. 2004;11:927-38 pubmed
    The monocyclic beta-lactam antibiotic nocardicin A is related structurally and biologically to the bicyclic beta-lactams comprised of penicillins/cephalosporins, clavams, and carbapenems...
  62. Jacoby G, Mills D, Chow N. Role of beta-lactamases and porins in resistance to ertapenem and other beta-lactams in Klebsiella pneumoniae. Antimicrob Agents Chemother. 2004;48:3203-6 pubmed
    ..From a wild-type strain producing ACT-1 beta-lactamase, ertapenem-resistant mutants for which the ertapenem MICs were up to 128 microg/ml and expression of outer membrane proteins was diminished could be selected...