Synthesis of (+)-crocacin D and simplified bioactive analogues.

Abstract:

:The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported.

journal_name

Bioorg Med Chem

authors

Pasqua AE,Ferrari FD,Crawford JJ,Whittingham WG,Marquez R

doi

10.1016/j.bmc.2015.01.008

subject

Has Abstract

pub_date

2015-03-01 00:00:00

pages

1062-8

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)00011-5

journal_volume

23

pub_type

杂志文章
  • Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.

    abstract::Emerging as an epidemic of the 21st century type 2 diabetes has become a major health problem throughout the globe. The number of deaths attributable to diabetes reflects the insufficient glycemic control achieved with the treatments used in recent past. DPP-4 inhibitors have been investigated as a new therapy with no...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2009.01.061

    authors: Havale SH,Pal M

    更新日期:2009-03-01 00:00:00

  • Citral derived amides as potent bacterial NorA efflux pump inhibitors.

    abstract::Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. au...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.05.030

    authors: Thota N,Koul S,Reddy MV,Sangwan PL,Khan IA,Kumar A,Raja AF,Andotra SS,Qazi GN

    更新日期:2008-07-01 00:00:00

  • Facile preparation of deuterium-labeled N-acylhomoserine lactones as internal standards for isotope dilution mass spectrometry.

    abstract::N-Acylhomoserine lactones (AHLs) are widely conserved signal molecules that mediate quorum sensing in Gram-negative bacteria. In this study, deuterium-labeled AHLs were prepared for use as internal standards for isotope dilution mass spectrometry. Their utility in the sensitive and precise quantification of AHLs in cu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.04.055

    authors: Kai K,Tani A,Hayashi H

    更新日期:2010-06-01 00:00:00

  • Synthesis and biological research of novel azaacridine derivatives as potent DNA-binding ligands and topoisomerase II inhibitors.

    abstract::DNA and DNA-related enzymes are one of the most effective and common used intracellular anticancer targets in clinic and laboratory studies, however, most of DNA-targeting drugs suffered from toxic side effects. Development of new molecules with good antitumor activity and low side effects is important. Based on compu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.04.030

    authors: Li D,Yuan Z,Chen S,Zhang C,Song L,Gao C,Chen Y,Tan C,Jiang Y

    更新日期:2017-07-01 00:00:00

  • Biaryl diacid inhibitors of human s-PLA2 with anti-inflammatory activity.

    abstract::Twenty-four hydrophobic dicarboxylic acids are described which were evaluated as inhibitors of 14 kDa human platelet phospholipase A2 (HP-PLA2). In general, biarylacetic acid derivatives were found to be more active than biaryl acids or biarylpropanoic acids. More potent inhibitors were obtained when hydrophobic group...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00047-x

    authors: Springer DM,Luh BY,Bronson JJ,McElhone KE,Mansuri MM,Gregor KR,Nettleton DO,Stanley PL,Tramposch KM

    更新日期:2000-05-01 00:00:00

  • Development of a highly selective EP2-receptor agonist. Part 1: identification of 16-hydroxy-17,17-trimethylene PGE2 derivatives.

    abstract::Design and synthesis of an EP2-receptor selective agonist began with the chemical modification of alpha- and omega-chains of butaprost 1a, which exhibits an affinity for the IP-receptor. Two series of prostaglandin (PG) analogues with a 16-hydroxy-17,17-trimethylene moiety as an omega-chain were identified. Among thos...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00369-8

    authors: Tani K,Naganawa A,Ishida A,Sagawa K,Harada H,Ogawa M,Maruyama T,Ohuchida S,Nakai H,Kondo K,Toda M

    更新日期:2002-04-01 00:00:00

  • Abenzyl 10-formyl-trideazafolic acid (abenzyl 10-formyl-TDAF): an effective inhibitor of glycinamide ribonucleotide transformylase.

    abstract::The synthesis of N-[7-(2-amino-3,4-dihydro-4-oxo-quinazolin-6-yl) -6-formyl-1-oxo-heptyl]-L-glutamic acid (2, abenzyl 10-formyl-5,8,10-trideazafolic acid) as a potential enzyme-assembled tight binding inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) or aminoimidazole carboxamide ribonucleotide transf...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(97)00123-5

    authors: Boger DL,Haynes NE,Warren MS,Ramcharan J,Marolewski AE,Kitos PA,Benkovic SJ

    更新日期:1997-09-01 00:00:00

  • Synthesis, biological activities and pharmacokinetic properties of new fluorinated derivatives of selective PDE4D inhibitors.

    abstract::A new series of selective PDE4D inhibitors has been designed and synthesized by replacing 3-methoxy group with 3-difluoromethoxy isoster moiety in our previously reported cathecolic structures. All compounds showed a good PDE4D3 inhibitory activity, most of them being inactive toward other PDE4 isoforms (PDE4A4, PDE4B...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.04.027

    authors: Brullo C,Massa M,Villa C,Ricciarelli R,Rivera D,Pronzato MA,Fedele E,Barocelli E,Bertoni S,Flammini L,Bruno O

    更新日期:2015-07-01 00:00:00

  • Evaluation of 1,2,5-thiadiazoles as modulators of M₁/M₅ muscarinic receptor subtypes.

    abstract::Studies have demonstrated the presence of allosteric binding sites on each of the muscarinic acetylcholine receptor (mAChR) subtypes. Since most drugs targeting muscarinic receptors bind to the highly conserved orthosteric binding site, they fail to achieve appreciable subtype selectivity. Targeting non-conserved allo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.01.049

    authors: Maheshwari A,Rao PS,Messer WS Jr

    更新日期:2014-03-15 00:00:00

  • The evaluation of quinonoid compounds against Trypanosoma cruzi: synthesis of imidazolic anthraquinones, nor-beta-lapachone derivatives and beta-lapachone-based 1,2,3-triazoles.

    abstract::In continuing our screening program of naphthoquinone activity against Trypanosoma cruzi, the aetiological agent of Chagas' disease, new beta-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-beta-lapachones, 3-alkoxy-nor-beta-lapachones and imidazole anthraquinones were synthesised and evaluated against bloodstream tr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.03.029

    authors: da Silva EN Jr,Guimarães TT,Menna-Barreto RF,Pinto Mdo C,de Simone CA,Pessoa C,Cavalcanti BC,Sabino JR,Andrade CK,Goulart MO,de Castro SL,Pinto AV

    更新日期:2010-05-01 00:00:00

  • Nucleotide analogues containing 2-oxa-bicyclo[2.2.1]heptane and l-alpha-threofuranosyl ring systems: interactions with P2Y receptors.

    abstract::The ribose moiety of adenine nucleotide 3',5'-bisphosphate antagonists of the P2Y(1) receptor has been successfully substituted with a rigid methanocarba ring system, leading to the conclusion that the North (N) ring conformation is preferred in receptor binding. Similarly, at P2Y(2) and P2Y(4) receptors, nucleotides ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.07.067

    authors: Ohno M,Costanzi S,Kim HS,Kempeneers V,Vastmans K,Herdewijn P,Maddileti S,Gao ZG,Harden TK,Jacobson KA

    更新日期:2004-11-01 00:00:00

  • Simple molecular engineering of glycol nucleic acid: progression from self-pairing to cross-pairing with cDNA and RNA.

    abstract::The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosphodiester linker in GNA with somewhat rigid and shorter carbamat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.022

    authors: Bose T,Kumar VA

    更新日期:2014-11-01 00:00:00

  • Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.

    abstract::A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of beta-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemag...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.06.009

    authors: Lewin AH,Navarro HA,Mascarella SW

    更新日期:2008-08-01 00:00:00

  • Reactions of some cyclopentenones with selected cysteine derivatives and biological activities of the product thioethers.

    abstract::The conjugate addition reaction between glutathione, N-Boc-cysteine methyl ester, N-acetyl cysteine methyl ester and N-acetyl cysteine and several substituted cyclopentenones is described. The reversibility of this process was demonstrated by thio-adduct metathesis on treatment of the adduct with a different cysteinyl...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.03.061

    authors: Bickley JF,Ciucci A,Evans P,Roberts SM,Ross N,Santoro MG

    更新日期:2004-06-15 00:00:00

  • Spirooxindole-pyrrolidine heterocyclic hybrids promotes apoptosis through activation of caspase-3.

    abstract::A small library of spirooxindole-pyrrolidine hybrids have been synthesized for the first time in an ionic liquid, [bmim]Br in good to excellent yields employing a new class of non-stabilized azomethine ylides derived from isatin and tyrosine, a combination that has been rarely employed for the in situ generation of az...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.03.011

    authors: Kumar RS,Almansour AI,Arumugam N,Mohammad F,Kotresha D,Menéndez JC

    更新日期:2019-06-15 00:00:00

  • Yohimbine as a Starting Point to Access Diverse Natural Product-Like Agents with Re-programmed Activities against Cancer-Relevant GPCR Targets.

    abstract::G protein-coupled receptors (GPCRs) constitute the largest protein superfamily in the human genome. GPCRs play key roles in mediating a wide variety of physiological events including proliferation and cancer metastasis. Given the major roles that GPCRs play in mediating cancer growth, they present promising targets fo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115546

    authors: Paciaroni NG,Norwood VM 4th,Ratnayake R,Luesch H,Huigens RW 3rd

    更新日期:2020-07-15 00:00:00

  • Binding ability of a thymine-functionalized oligolysine towards nucleic acids.

    abstract::In this Letter, we investigated the binding properties towards nucleic acids of a thymine-functionalized oligolysine, composed of nucleobase-bearing amino acid moieties and underivatized l-lysine residues alternate in the backbone. The basic nucleopeptide proved to be well soluble in water and able to interact with bo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.12.053

    authors: Roviello GN,Musumeci D,D'Alessandro C,Pedone C

    更新日期:2014-02-01 00:00:00

  • Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides.

    abstract::We are investigating compounds that could be useful in the treatment of neoplastic lesions of the cervix by acting on the oncoprotein E6 of human papillomavirus-16. The E6 protein contains two potential zinc-binding domains that are required for most of its functions. We have published tests that measure (i) the relea...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00193-0

    authors: Beerheide W,Sim MM,Tan YJ,Bernard HU,Ting AE

    更新日期:2000-11-01 00:00:00

  • Synthesis, structural characterization and cell death-inducing effect of novel palladium(II) and platinum(II) saccharinate complexes with 2-(hydroxymethyl)pyridine and 2-(2-hydroxyethyl)pyridine on cancer cells in vitro.

    abstract::Four palladium(II) and platinum(II) saccharinate (sac) complexes with 2-(hydroxymethyl)pyridine (2-hmpy) and 2-(2-hydroxyethyl)pyridine (2-hepy), namely trans-[Pd(2-hmpy)2(sac)2]·H2O (1), trans-[Pt(2-hmpy)2(sac)2]·3H2O (2), trans-[Pd(2-hepy)2(sac)2] (3) and trans-[Pt(2-hepy)2(sac)2] (4), have been synthesized and char...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.08.050

    authors: Ari F,Aztopal N,Icsel C,Yilmaz VT,Guney E,Buyukgungor O,Ulukaya E

    更新日期:2013-11-01 00:00:00

  • Large scale preparation of chiral building blocks for the P3 site of renin inhibitors.

    abstract::Racemic ethyl 2-benzyl-3-(tert-butylsulfonyl)propionate (1) and racemic ethyl 2-benzyl-3-[[1-methyl-1-((morpholin-4-yl)carbonyl)ethyl]sulfonyl] propionate (3) were enantioselectively hydrolyzed by subtilisin Carlsberg generating the respective (S)-acids used as building blocks for renin inhibitors. The esters were rea...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(94)80007-3

    authors: Doswald S,Estermann H,Kupfer E,Stadler H,Walther W,Weisbrod T,Wirz B,Wostl W

    更新日期:1994-06-01 00:00:00

  • N-phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents.

    abstract::A range of N-phenethyl, N-phenacyl, and N-(1- and 2-naphthylmethyl) derivatives of 5,7-dibromoisatin 2 were prepared by N-alkylation reactions. Their activity against human monocyte-like histiocytic lymphoma (U937), leukemia (Jurkat), and breast carcinoma (MDA-MB-231) cell lines was assessed. The results allowed furth...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.12.026

    authors: Matesic L,Locke JM,Bremner JB,Pyne SG,Skropeta D,Ranson M,Vine KL

    更新日期:2008-03-15 00:00:00

  • Predicting multiple drugs side effects with a general drug-target interaction thermodynamic Markov model.

    abstract::Most of present molecular descriptors just consider the molecular structure. In the present article we pretend extending the use of Markov chain models to define novel molecular descriptors, which consider in addition to molecular structure other parameters like target site or toxic effect. Specifically, this molecula...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.11.030

    authors: González-Díaz H,Cruz-Monteagudo M,Molina R,Tenorio E,Uriarte E

    更新日期:2005-02-15 00:00:00

  • Synthesis and biological evaluation of novel pyrazolyl-2,4-thiazolidinediones as anti-inflammatory and neuroprotective agents.

    abstract::Novel pyrazolyl-2,4-thiazolidinediones were prepared via the reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinediones and substituted benzyl-2,4-thiazolidinediones. The resultant compounds were first evaluated for their anti-inflammatory and neuroprotective properties in vitro. The active compounds ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.01.021

    authors: Youssef AM,White MS,Villanueva EB,El-Ashmawy IM,Klegeris A

    更新日期:2010-03-01 00:00:00

  • Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage.

    abstract::An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, rat liver homogenate lipid ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.03.032

    authors: Gong J,Huang K,Wang F,Yang L,Feng Y,Li H,Li X,Zeng S,Wu X,Stöckigt J,Zhao Y,Qu J

    更新日期:2009-05-01 00:00:00

  • Design, synthesis and anti-P. falciparum activity of pyrazolopyridine-sulfonamide derivatives.

    abstract::Ten 1-phenyl-1H-pyrazolo[3,4-b]pyridine derivatives connected by a linker group to benzenesulfonamide moieties with different substituents in the 4-position were synthesized and assayed against Plasmodium falciparum. These ten compounds exhibited activity in vitro against the chloroquine-resistant clone W2 with IC50 v...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.07.049

    authors: Silva TB,Bernardino AMR,Ferreira MLG,Rogerio KR,Carvalho LJM,Boechat N,Pinheiro LCS

    更新日期:2016-09-15 00:00:00

  • Syntheses, biochemical and biological evaluation of staurosporine analogues from the microbial metabolite rebeccamycin.

    abstract::The indolocarbazole antibiotics staurosporine and rebeccamycin (1) are potent antitumor drugs targeting protein kinase C and topoisomerase I, respectively. To obtain staurosporine analogues from rebeccamycin, different structural modifications were performed: coupling of the sugar moiety to the second indole nitrogen,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00096-0

    authors: Anizon F,Moreau P,Sancelme M,Voldoire A,Prudhomme M,Ollier M,Sevère D,Riou JF,Bailly C,Fabbro D,Meyer T,Aubertin AM

    更新日期:1998-09-01 00:00:00

  • Actin-binding doliculide causes premature senescence in p53 wild type cells.

    abstract::Addressing the actin cytoskeleton as future anticancer target can be an innovative chemotherapeutic approach to combat malignancies. Doliculide is a potent stabilizer of actin filaments and can be used as tool and therapeutic lead in cancer research. Though a variety of molecules are known to bind to actin and lead to...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.11.042

    authors: Foerster F,Chen T,Altmann KH,Vollmar AM

    更新日期:2016-01-15 00:00:00

  • Downsizing of an HIV-cell fusion inhibitor, T22 ([Tyr5,12, Lys7]-polyphemusin II), with the maintenance of anti-HIV activity and solution structure.

    abstract::T22 ([Tyr5,12,Lys7]-polyphemusin II) has been shown to have strong anti-human immunodeficiency virus (HIV) activity comparable to that of 3'-azido-2',3'-dideoxythymidine (AZT). T22, an 18-residue peptide amide, takes an antiparallel beta-sheet structure that is maintained by two disulfide bridges. Herein we synthesize...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(97)10055-4

    authors: Tamamura H,Waki M,Imai M,Otaka A,Ibuka T,Waki K,Miyamoto K,Matsumoto A,Murakami T,Nakashima H,Yamamoto N,Fujii N

    更新日期:1998-04-01 00:00:00

  • Discovery of novel quinoline-based mTOR inhibitors via introducing intra-molecular hydrogen bonding scaffold (iMHBS): The design, synthesis and biological evaluation.

    abstract::A series of quinoline derivatives featuring the novelty of introducing intra-molecular hydrogen bonding scaffold (iMHBS) were designed, synthesized and biologically evaluated for their mTOR inhibitory activity, as well as anti-proliferative efficacies against HCT-116, PC-3 and MCF-7 cell lines. As a result, six compou...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.11.003

    authors: Ma X,Lv X,Qiu N,Yang B,He Q,Hu Y

    更新日期:2015-12-15 00:00:00

  • Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells.

    abstract::Solid-phase synthesis of a small combinatorial library of dihydroceramide analogues as mixtures of erythro and threo diastereomers is described. Some dihydroceramide analogues cause growth arrest and apoptosis in a dose-dependent manner in human alveolar epithelial cells. This activity is likely due to the threo isome...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.10.024

    authors: Villorbina G,Canals D,Carde L,Grijalvo S,Pascual R,Rabal O,Teixidó J,Fabriàs G,Llebaria A,Casas J,Delgado A

    更新日期:2007-01-01 00:00:00