Enantioselective synthesis of (+)-4-demethoxy-1,4-dimethyldaunomycinone.

Abstract:

:(+)-4-Demethoxy-1,4-dimethyldaunomycinone 1 was synthesized using a convergent approach. Here, the key tetracyclic compound 10 was assembled by way of a Diels-Alder reaction using the sugar-based diene 8 and the quinizarin-related dienophile 7.

journal_name

Bioorg Med Chem

authors

Kotha S,Stoodley RJ

doi

10.1016/s0968-0896(01)00316-9

subject

Has Abstract

pub_date

2002-03-01 00:00:00

pages

621-4

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968089601003169

journal_volume

10

pub_type

杂志文章
  • Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives.

    abstract::N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.02.024

    authors: Chen S,Fahmi NE,Nangreave RC,Mehellou Y,Hecht SM

    更新日期:2012-04-15 00:00:00

  • Isolation of antiplasmodial anthraquinones from Kniphofia ensifolia, and synthesis and structure-activity relationships of related compounds.

    abstract::Bioassay-guided separation of the South African plant Kniphofia ensifolia for antiplasmodial activity led to the isolation of two new anthraquinones, named kniphofiones A and B (3 and 4), together with three known bioactive anthraquinone monomers (1, 2 and 5), and four known bisanthraquinones (6-9). The structures of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.11.032

    authors: Dai Y,Harinantenaina L,Bowman JD,Da Fonseca IO,Brodie PJ,Goetz M,Cassera MB,Kingston DG

    更新日期:2014-01-01 00:00:00

  • Structure-activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling.

    abstract::A series of salicylanilides was synthesized based on a high-throughput screening hit against Mycobacterium tuberculosis. A free phenolic hydroxyl on the salicylic acid moeity is required for activity, and the structure-activity relationship of the aniline ring is largely driven by the presence of electron withdrawing ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.10.056

    authors: Lee IY,Gruber TD,Samuels A,Yun M,Nam B,Kang M,Crowley K,Winterroth B,Boshoff HI,Barry CE 3rd

    更新日期:2013-01-01 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

  • Synthesis, biological evaluation and molecular modeling study of 2-amino-3,5-disubstituted-pyrazines as Aurora kinases inhibitors.

    abstract::Serine/threonine protein kinases Aurora A, B, and C play essential roles in cell mitosis and cytokinesis, and a number of Aurora kinase inhibitors have been evaluated in the clinic. Herein we report the synthesis and their antiproliferation of 3,5-disubstituted-2-aminopyrazines as kinases inhibitors. Amongst, 4-((3-am...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115351

    authors: Bo YX,Xiang R,Xu Y,Hao SY,Wang XR,Chen SW

    更新日期:2020-03-01 00:00:00

  • Novel synthetic 2-amino-10-(3,5-dimethoxy)benzyl-9(10H)-acridinone derivatives as potent DNA-binding antiproliferative agents.

    abstract::A series of novel 9(10H)-acridinone derivatives with terminal amino substituents at C2 position on the acridinone ring were synthesized and studied for their antiproliferative activity and underlying mechanisms. These compounds demonstrated promising cytotoxicity to leukemia cells CCRF-CEM, displaying IC(50) values in...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.08.058

    authors: Gao C,Liu F,Luan X,Tan C,Liu H,Xie Y,Jin Y,Jiang Y

    更新日期:2010-11-01 00:00:00

  • Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest.

    abstract::Bioassay-directed fractionation of the leaf and root extracts of the antiproliferative Madagascar plant Stuhlmannia moavi afforded 6-acetyl-5,8-dihydroxy-2-methoxy-7-methyl-1,4-naphthoquinone (stuhlmoavin, 1) as the most active compound, with an IC50 value of 8.1 μM against the A2780 human ovarian cancer cell line, as...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.10.038

    authors: Liu Y,Harinantenaina L,Brodie PJ,Bowman JD,Cassera MB,Slebodnick C,Callmander MW,Randrianaivo R,Rakotobe E,Rasamison VE,Applequist W,Birkinshaw C,Lewis GP,Kingston DG

    更新日期:2013-12-15 00:00:00

  • Solid phase synthesis and antiprotozoal evaluation of di- and trisubstituted 5'-carboxamidoadenosine analogues.

    abstract::The rapid increase of resistance to drugs commonly used in the treatment of tropical diseases such as malaria and African sleeping sickness calls for the prompt development of new safe and efficacious drugs. The pathogenic protozoan parasites lack the capability of synthesising purines de novo and they take up preform...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.10.011

    authors: Rodenko B,Detz RJ,Pinas VA,Lambertucci C,Brun R,Wanner MJ,Koomen GJ

    更新日期:2006-03-01 00:00:00

  • Stereostructure-based differences in the interactions of cardiotoxic local anesthetics with cholesterol-containing biomimetic membranes.

    abstract::Amide-type pipecoloxylidide local anesthetics, bupivacaine, and ropivacaine, show cardiotoxic effects with the potency depending on stereostructures. Cardiotoxic drugs not only bind to cardiomyocyte membrane channels to block them but also modify the physicochemical property of membrane lipid bilayers in which channel...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.04.030

    authors: Tsuchiya H,Ueno T,Mizogami M

    更新日期:2011-06-01 00:00:00

  • Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH.

    abstract::The boronic acid group is widely used in chemosensor design due to its ability to reversibly bind diol-containing compounds. The thermodynamic properties of the boronic acid-diol binding process have been investigated extensively. However, there are few studies of the kinetic properties of such binding processes. In t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.03.014

    authors: Ni N,Laughlin S,Wang Y,Feng Y,Zheng Y,Wang B

    更新日期:2012-05-01 00:00:00

  • Novel dimeric aryldiketo containing inhibitors of HIV-1 integrase: effects of the phenyl substituent and the linker orientation.

    abstract::Aryl diketoacids (ADK) and their bioisosteres are among the most promising HIV-1 integrase (IN) inhibitors. Previously, we designed a series of ADK dimers as a new class of IN inhibitors that were hypothesized to target two divalent metal ions on the active site of IN. Herein we present a further structure-activity re...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.07.008

    authors: Zeng LF,Jiang XH,Sanchez T,Zhang HS,Dayam R,Neamati N,Long YQ

    更新日期:2008-08-15 00:00:00

  • Synthesis and characterizations of novel quinoline derivatives having mixed ligand activities at the kappa and mu receptors: Potential therapeutic efficacy against morphine dependence.

    abstract::Based on an established 3D pharmacophore, a series of quinoline derivatives were synthesized. The opioidergic properties of these compounds were determined by a competitive binding assay using (125)I-Dynorphine, (3)H-DAMGO and (125)I-DADLE for kappa, mu, and delta receptors, respectively. Results showed varying degree...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.07.024

    authors: Deb I,Paira P,Hazra A,Banerjee S,Dutta PK,Mondal NB,Das S

    更新日期:2009-08-15 00:00:00

  • Synthesis of benzoxazole derivatives as interleukin-6 antagonists.

    abstract::A growing number of studies have demonstrated that interleukin (IL)-6 plays pathological roles in the development of chronic inflammatory disease and autoimmune disease by activating innate immune cells and by stimulating adaptive inflammatory T cells. So, suppression of IL-6 function may be beneficial for prevention ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.03.072

    authors: Kim D,Won HY,Hwang ES,Kim YK,Choo HP

    更新日期:2017-06-15 00:00:00

  • Synthesis and evaluation of antitumoral activity of ester and amide derivatives of 2-arylamino-6-trifluoromethyl-3-pyridinecarboxylic acids.

    abstract::The synthesis and antitumoral activity of ester and amide derivatives of 2-arylamino-6-trifluoromethyl-3-pyridinecarboxylic acids 8-58 is described. Trifluoromethylpyridine derivatives 8-58 were evaluated for their anticancer activity toward human tumoral cell lines by the National Cancer Institute (NCI). Most of them...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.11.069

    authors: Onnis V,Cocco MT,Lilliu V,Congiu C

    更新日期:2008-03-01 00:00:00

  • Selection of genomic target RNAs by iterative screening.

    abstract::A growing number of proteins are known to exert their regulatory or biological functions via RNA binding. In some cases genetic interactions allow us to infer candidate targets for RNA directed regulation, but in many other cases identification of potential regulatory targets is problematic. We have developed an in vi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00029-3

    authors: Brunel C,Ehresmann B,Ehresmann C,McKeown M

    更新日期:2001-10-01 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

  • Pleuromutilins. Part 1. The identification of novel mutilin 14-carbamates.

    abstract::A novel series of mutilin 14-carbamates has been discovered as a result of structure-activity studies on the naturally occurring antibiotic pleuromutilin (1). In particular, the 4-methoxybenzoylcarbamate, SB-222734 (15o) displays potent antibacterial activity against a number of bacterial pathogens which are resistant...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00338-2

    authors: Brooks G,Burgess W,Colthurst D,Hinks JD,Hunt E,Pearson MJ,Shea B,Takle AK,Wilson JM,Woodnutt G

    更新日期:2001-05-01 00:00:00

  • Separation of alpha-adrenergic and imidazoline/guanidinium receptive sites (IGRS) activity in a series of imidazoline analogues of cirazoline.

    abstract::To characterize the structure-activity relationship between alpha 1-adrenergic receptors and the family of imidazoline/guanidinium receptive sites (IGRS), we synthesized and characterized a series of analogues of cirazoline, an imidazoline with high affinity for alpha 1-adrenergic receptors and IGRS. Analysis of poten...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00132-z

    authors: Brasili L,Pigini M,Marucci G,Quaglia W,Malmusi L,Lanier SM,Lanier B

    更新日期:1995-11-01 00:00:00

  • Estimation of hERG inhibition of drug candidates using multivariate property and pharmacophore SAR.

    abstract::We describe the development of a computational model for the prediction of the inhibition of K(+) flow through the hERG ion channel. Using a collection of 1075 discovery compounds with hERG inhibition measured in our standard patch-clamp electrophysiology assay, molecular features important for drug-induced inhibition...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.06.028

    authors: Johnson SR,Yue H,Conder ML,Shi H,Doweyko AM,Lloyd J,Levesque P

    更新日期:2007-09-15 00:00:00

  • Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity.

    abstract::A type of novel α,β-unsaturated cyclohexanone analogous, which designed based on the curcumin core structure, have been discovered as potential EGFR inhibitors. These compounds exhibit potent antiproliferative activity in two human tumor cell lines (Hep G2 and B16-F10). Among them, compounds I(3) and I(12) displayed t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.11.031

    authors: Xu YY,Cao Y,Ma H,Li HQ,Ao GZ

    更新日期:2013-01-15 00:00:00

  • Synthesis and biological evaluation of novel flexible nucleoside analogues that inhibit flavivirus replication in vitro.

    abstract::Flaviviruses, such as Dengue (DENV) and Zika (ZIKV) viruses, represent a severe health burden. There are currently no FDA-approved treatments, and vaccines against most flaviviruses are still lacking. We have developed several flexible analogues ("fleximers") of the FDA-approved nucleoside Acyclovir that exhibit activ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115713

    authors: Thames JE,Waters CD 3rd,Valle C,Bassetto M,Aouadi W,Martin B,Selisko B,Falat A,Coutard B,Brancale A,Canard B,Decroly E,Seley-Radtke KL

    更新日期:2020-08-31 00:00:00

  • α-Glucosidase inhibition activity and in silico study of 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one, a synthetic derivative of flavone.

    abstract::A synthetic flavone derivative 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one (BDC) was synthesized by the one pot reaction method and assessed for α-glucosidase inhibitory activity. The BDC demonstrated dose dependent inhibition of α-glucosidase activity. A maximum inhibition (99.3 ± 0.26%) of α-glucosidase was observ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.12.021

    authors: Meena SN,Kumar U,Naik MM,Ghadi SC,Tilve SG

    更新日期:2019-06-15 00:00:00

  • Pyridine alkaloids with activity in the central nervous system.

    abstract::This review discusses all pyridine alkaloids with CNS activity, their therapeutic potential, and the interesting array of sources whence they originate. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115820

    authors: Lin SX,Curtis MA,Sperry J

    更新日期:2020-12-15 00:00:00

  • 2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance.

    abstract::Gangjee et al. recently reported a novel series of 2-amino-4-methyl-5-phenylethyl substituted-7-benzyl-pyrrolo[2,3-d]pyrimidines, some of which exhibited two digit nanomolar antitumor and antimitotic activity and were not subject to P-glycoprotein (Pgp) or multidrug resistance protein 1 (MRP1) mediated tumor resistanc...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.05.030

    authors: Gangjee A,Namjoshi OA,Keller SN,Smith CD

    更新日期:2011-07-15 00:00:00

  • Probing linker design in citric acid-ciprofloxacin conjugates.

    abstract::A series of structurally related citric acid-ciprofloxacin conjugates was synthesised to investigate the influence of the linker between citric acid and ciprofloxacin on antibacterial activities. Minimum inhibitory concentrations (MICs) were determined against a panel of reference strains and clinical isolates of bact...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.04.009

    authors: Milner SJ,Snelling AM,Kerr KG,Abd-El-Aziz A,Thomas GH,Hubbard RE,Routledge A,Duhme-Klair AK

    更新日期:2014-08-15 00:00:00

  • Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents.

    abstract::A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the mos...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.02.028

    authors: Wang G,Li C,He L,Lei K,Wang F,Pu Y,Yang Z,Cao D,Ma L,Chen J,Sang Y,Liang X,Xiang M,Peng A,Wei Y,Chen L

    更新日期:2014-04-01 00:00:00

  • Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives.

    abstract::3-Aryl-4-formylsydnone 4'-phenylthiosemicarbazones (3a-d) and 3-aryl-4-formylsydnone thiosemicarbazones (3e-h), which are precursors of 3-aryl-4-heterocyclic sydnones, are prepared by the condensation of 3-aryl-4-formylsydnones (1a-d) with 4'-phenylthiosemicarbazide (2a) and thiosemicarbazide (2b), respectively. The t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.06.033

    authors: Shih MH,Ke FY

    更新日期:2004-09-01 00:00:00

  • Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARalpha.

    abstract::Pterostilbene, a naturally occurring analog of resveratrol, has previously shown PPARalpha activation in H4IIEC3 cells and was found to decrease cholesterol levels in animals. In this study, analogs of pterostilbene were synthesized and their ability to activate PPARalpha was investigated. Among analogs that was synth...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.01.051

    authors: Mizuno CS,Ma G,Khan S,Patny A,Avery MA,Rimando AM

    更新日期:2008-04-01 00:00:00

  • Palladium(II) saccharinate complexes with bis(2-pyridylmethyl)amine induce cell death by apoptosis in human breast cancer cells in vitro.

    abstract::The outcomes of breast cancer patients are still poor although new compounds have recently been introduced into the clinic. Therefore, novel chemical approaches are required. In the present study, palladium(II) and corresponding platinum(II) complexes containing bis(2-pyridylmethyl)amine (bpma) and saccharine were syn...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.03.073

    authors: Ari F,Ulukaya E,Sarimahmut M,Yilmaz VT

    更新日期:2013-06-01 00:00:00

  • Stereoselective synthesis and anti-inflammatory activities of 6- and 7-membered dioxacycloalkanes.

    abstract::A class of 5-trifluoroacetylamino-1,3-dioxacycloalkanes, 5-benzoylamino-1,3-dioxacycloalkanes, and 5-amino-1,3-dioxacycloalkane compounds were stereoselectively synthesized as potential anti-inflammatory drug candidates. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.09.068

    authors: Gu K,Bi L,Zhao M,Wang C,Dolan C,Kao MC,Tok JB,Peng S

    更新日期:2006-03-01 00:00:00