当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax.

Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax.

Abstract：

:A novel glycosphingolipid, beta-D-GalNAcp(1-->4)[alpha-D- Fucp(1-->3)]-beta-D-GlcNAcp(1-->)Cer (1), isolated from the marine sponge Aplysinella rhax, has a unique structure, with D-fucose and N-acetyl-D-galactosamine attached to a reducing-end N-acetyl-D-glucosamine through an alpha1-->3 and beta1-->4 linkage, respectively. We synthesized glycolipid analogues carrying a 2-branched fatty alkyl residue or a 2-trimethylsilyl ethyl residue in place of ceramide (2 and 3), non-natural type trisaccharide analogue containing an L-fucose residue (4), and other analogues (5 and 6). Among these prepared compounds, 2 showed the most potent nitric oxide (NO) production inhibitory activity against LPS-activated J774.1 cells. In addition, their structure-activity relationships were established.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Hada N,Nakashima T,Shrestha SP,Masui R,Narukawa Y,Tani K,Takeda T

doi

10.1016/j.bmcl.2007.07.108

subject

Has Abstract

pub_date

2007-11-01 00:00:00

pages

5912-5

issue

21

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(07)00913-4

journal_volume

17

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • Evaluation of series of isobenzofuranone dimers as PKCalpha ligands: implication for the distance between the two ligand binding sites.

    abstract：:Protein kinase C (PKC) is a family of enzymes, which play important roles in intracellular signal transduction. To examine the distance between the two ligand binding sites (C1A and C1B) of PKC, we designed and synthesized two series of isobenzofuranone dimers. Peak binding activities were observed for the C3-acyl cha...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.02.098

    authors： Baba Y,Mayumi S,Hirai G,Kawasaki H,Ogoshi Y,Yanagisawa T,Hashimoto Y,Sodeoka M

    更新日期：2004-06-07 00:00:00

  • TR-FRET binding assay targeting unactivated form of Bruton's tyrosine kinase.

    abstract：:Bruton's Tyrosine Kinase (BTK) is one of the crucial kinases for the B cell maturation and mast cell activation, and specific inhibitors of BTK are considered to be attractive targets in drug discovery research. In this Letter, we have designed and synthesized a new fluorescent probe for TR-FRET-based high-throughput ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.04.001

    authors： Asami T,Kawahata W,Sawa M

    更新日期：2015-01-01 00:00:00

  • Novel endoperoxides: synthesis and activity against Candida species.

    abstract：:Fifteen new endoperoxides have been synthesised and tested for activity against pathogenic Candida species. These endoperoxides can be prepared in high yields, in one to three steps, from inexpensive starting materials. Despite chemical and structural similarities, their inhibitory activity against Candida growth vari...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.10.101

    authors： Macreadie P,Avery T,Greatrex B,Taylor D,Macreadie I

    更新日期：2006-02-15 00:00:00

  • Novel triclabendazole prodrug: A highly water soluble alternative for the treatment of fasciolosis.

    abstract：:In this work we present the synthesis, aqueous solubility and stability, hydrolysis by alkaline phosphatase, and in vivo fasciolicidal activity in sheep of a highly water soluble phosphate salt prodrug of triclabendazole (MFR-5). The aqueous solubility of MFR-5 at pH 7 was 88,000-fold that of triclabendazole. MFR-5 sh...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.12.004

    authors： Flores-Ramos M,Ibarra-Velarde F,Jung-Cook H,Hernández-Campos A,Vera-Montenegro Y,Castillo R

    更新日期：2017-02-01 00:00:00

  • 4-(Alkylthio)- and 4-(arylthio)-benzonitrile derivatives as androgen receptor antagonists for the topical suppression of sebum production.

    abstract：:The first examples of thioether-substituted benzonitriles as potential soft-drug androgen receptor antagonists are reported. A number of 4-(alkylthio)- and of 4-(arylthio)-benzonitrile analogs were evaluated in human androgen receptor binding and cellular functional assays. Analogs with potent in vitro binding and cel...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.01.063

    authors： Mitchell L,Wang Z,Hu LY,Kostlan C,Carroll M,Dettling D,Du D,Pocalyko D,Wade K

    更新日期：2009-03-01 00:00:00

  • Double stranded DNA discrimination by di-pyrene modified gamma-cyclodextrin.

    abstract：:Neutral fluorescent active di-pyrene modified gamma-cyclodextrin (1) was synthesized in order to discriminate with single and double strand DNA (ssDNA and dsDNA, respectively) with high selectivity. The binding and selectivity of 1 for dsDNA was indicated by increase of the fluorescent intensity in an addition of dsDN...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.04.066

    authors： Takeda A,Akimoto K,Kondo Y,Hamada F

    更新日期：2010-06-01 00:00:00

  • Design and synthesis of 3-substituted benzamide derivatives as Bcr-Abl kinase inhibitors.

    abstract：:A series of 3-substituted benzamide derivatives structurally related to STI-571 (imatinib mesylate), a Bcr-Abl tyrosine kinase inhibitor used to treat chronic myeloid leukemia (CML), was prepared and evaluated for antiproliferative activity against the Bcr-Abl-positive leukemia cell line K562. About ten 3-halogenated ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.11.042

    authors： Asaki T,Sugiyama Y,Hamamoto T,Higashioka M,Umehara M,Naito H,Niwa T

    更新日期：2006-03-01 00:00:00

  • Modeling directed design and biological evaluation of quinazolinones as non-peptidic growth hormone secretagogues.

    abstract：:Quinazolinone derivatives were synthesized and evaluated as non-peptidic growth hormone secretagogues. Modeling guided design of quinazolinone compound 21 led to a potency enhancement of greater than 200-fold compared to human growth hormone secretagogue affinity of a screening lead 4. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00584-3

    authors： Ye Z,Gao Y,Bakshi RK,Chen MH,Rohrer SP,Feighner SD,Pong SS,Howard AD,Blake A,Birzin ET,Locco L,Parmar RM,Chan WW,Schaeffer JM,Smith RG,Patchett AA,Nargund RP

    更新日期：2000-01-03 00:00:00

  • Triple recognition of B-DNA.

    abstract：:A novel conjugate of Hoechst 33258, pyrene and neomycin was synthesized and examined for its binding and stabilization of A-T rich DNA duplexes using spectroscopic and viscometric techniques. The conjugate, containing three well known ligands that bind nucleic acids albeit in different binding modes, was found to sign...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.07.079

    authors： Willis B,Arya DP

    更新日期：2009-09-01 00:00:00

  • Synthesis of novel amide functionalized 2H-chromene derivatives by Ritter amidation of primary alcohol using HBF4·OEt2 as a mild and versatile reagent and evaluation of their antimicrobial and anti-biofilm activities.

    abstract：:A series of novel amide functionalized 2H-chromene derivatives 3 were prepared starting from ethyl-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 1 via sodium borohydride reduction followed by Ritter amidation using HBF4·OEt2 as a mild and versatile reagent. All the products 3 were screened for antimicrobial ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.05.041

    authors： Ratnakar Reddy K,Poornachandra Y,Jitender Dev G,Mallareddy G,Nanubolu JB,Kumar CG,Narsaiah B

    更新日期：2015-08-01 00:00:00

  • Development of clickable active site-directed photoaffinity probes for γ-secretase.

    abstract：:We have developed clickable active site-directed photoaffinity probes for γ-secretase which incorporate a photoreactive benzophenone group and an alkyne handle for subsequent click chemistry mediated conjugation with azide-linked reporter tags for visualization (e.g., TAMRA-azide) or enrichment (e.g., biotin-azide) of...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.02.027

    authors： Crump CJ,am Ende CW,Ballard TE,Pozdnyakov N,Pettersson M,Chau DM,Bales KR,Li YM,Johnson DS

    更新日期：2012-04-15 00:00:00

  • A three-step protocol for lead optimization: quick identification of key conformational features and functional groups in the SAR studies of non-ATP competitive MK2 (MAPKAPK2) inhibitors.

    abstract：:A three-step protocol for SAR development was introduced and applied to the SAR studies of the MK2 inhibitor program. Following this protocol, key conformational features and functional groups for improving MK2 inhibitor activity were quickly identified. Through this effort, the initial gap observed between in vitro b...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.11.074

    authors： Huang X,Zhu X,Chen X,Zhou W,Xiao D,Degrado S,Aslanian R,Fossetta J,Lundell D,Tian F,Trivedi P,Palani A

    更新日期：2012-01-01 00:00:00

  • Pyridazines. Part 36: Synthesis and antiplatelet activity of 5-substituted-6-phenyl-3(2H)-pyridazinones.

    abstract：:A convenient and efficient palladium-catalysed retro-ene-assisted method has been developed to prepare a series of 5-substituted-6-phenyl-3(2H)-pyridazinones as potential antiplatelet drugs. The most active compounds were those that contain a 3-phenyl-3-oxo-propenyl fragment or a phenylthio group at position 5 of the ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2003.11.009

    authors： Coelho A,Sotelo E,Fraiz N,Yáñez M,Laguna R,Cano E,Raviña E

    更新日期：2004-01-19 00:00:00

  • Multidrug resistance-reversal effects of resin glycosides from Dichondra repens.

    abstract：:Investigation of hydrophobic extract of Dichondra repens (Convolvulaceae) led to the isolation of three new resin glycosides dichondrins A-C (1-3), and three known resin glycosides cus-1, cus-2, and cuse 3. All the isolated resin glycosides with an acyclic core were evaluated for their multidrug resistance reversal ac...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.12.083

    authors： Song WB,Wang WQ,Zhang SW,Xuan LJ

    更新日期：2015-02-15 00:00:00

  • CC chemokine receptor-3 (CCR3) antagonists: improving the selectivity of DPC168 by reducing central ring lipophilicity.

    abstract：:DPC168, a benzylpiperidine-substituted aryl urea CCR3 antagonist evaluated in clinical trials, was a relatively potent inhibitor of the 2D6 isoform of cytochrome P-450 (CYP2D6). Replacement of the cyclohexyl central ring with saturated heterocycles provided potent CCR3 antagonists with improved selectivity against CYP...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.03.065

    authors： Pruitt JR,Batt DG,Wacker DA,Bostrom LL,Booker SK,McLaughlin E,Houghton GC,Varnes JG,Christ DD,Covington M,Das AM,Davies P,Graden D,Kariv I,Orlovsky Y,Stowell NC,Vaddi KG,Wadman EA,Welch PK,Yeleswaram S,Solomon KA

    更新日期：2007-06-01 00:00:00

  • Design of selective Cathepsin inhibitors.

    abstract：:A number of molecular recognition features have been exploited in structure-based design of selective Cathepsin inhibitors. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.06.090

    authors： Bethel PA,Gerhardt S,Jones EV,Kenny PW,Karoutchi GI,Morley AD,Oldham K,Rankine N,Augustin M,Krapp S,Simader H,Steinbacher S

    更新日期：2009-08-15 00:00:00

  • Identification and optimisation of a series of substituted 5-pyridin-2-yl-thiophene-2-hydroxamic acids as potent histone deacetylase (HDAC) inhibitors.

    abstract：:Further investigation of a series of thienyl-based hydroxamic acids that included ADS100380 and ADS102550 led to the identification of the 5-pyridin-2-yl-thiophene-2-hydroxamic acid 3c, which possessed modest HDAC inhibitory activity. Substitution at the 5- and 6-positions of the pyridyl ring of compound 3c provided c...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.10.045

    authors： Price S,Bordogna W,Braganza R,Bull RJ,Dyke HJ,Gardan S,Gill M,Harris NV,Heald RA,van den Heuvel M,Lockey PM,Lloyd J,Molina AG,Roach AG,Roussel F,Sutton JM,White AB

    更新日期：2007-01-15 00:00:00

  • Aminocyclohexylsulfonamides: discovery of metabolically stable alpha(1a/1d)-selective adrenergic receptor antagonists for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS).

    abstract：:Benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS) can be effectively treated by alpha(1) adrenergic receptor antagonists, but these drugs also produce side effects that are related to their subtype non-selective nature. To overcome this limitation, it was hypothesized that an alpha(1a/1d) subtype-se...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.09.051

    authors： Chiu G,Li S,Cai H,Connolly PJ,Peng S,Stauber K,Pulito V,Liu J,Middleton SA

    更新日期：2007-11-15 00:00:00

  • Discovery of a novel series of selective HCN1 blockers.

    abstract：:The discovery of a series of novel, potent, and selective blockers of the cyclic nucleotide-modulated channel HCN1 is disclosed. Here we report an SAR study around a series of selective blockers of the HCN1 channel. Utilization of a high-throughput VIPR assay led to the identification of a novel series of 2,2-disubsti...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.07.051

    authors： McClure KJ,Maher M,Wu N,Chaplan SR,Eckert WA 3rd,Lee DH,Wickenden AD,Hermann M,Allison B,Hawryluk N,Breitenbucher JG,Grice CA

    更新日期：2011-09-15 00:00:00

  • Polymer-supported catalysts: enantioselective hydrogenation and hydrogen transfer reduction.

    abstract：:Different types of heterogenized catalysts were involved in asymmetric reactions. Hydrogen transfer reduction was performed with amino alcohols derived from poly((S)-(GMA-co-EGDMA or DVB)) and hydrogenation with BINAP grafted onto PEG or copolymerized with isocyanates as ligands. Attempts of catalysts recycling are re...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00258-5

    authors： Saluzzo C,Lamouille T,Hérault D,Lemaire M

    更新日期：2002-07-22 00:00:00

  • Colorectal anticancer activities of polymethoxylated 3-naphthyl-5-phenylpyrazoline-carbothioamides.

    abstract：:To develop potent chemotherapeutic agents for treating colorectal cancers, polymethoxylated 3-naphthyl-5-phenylpyrazoline-carbothioamide derivatives were designed. Twenty-two novel derivatives were synthesized and their cytotoxicities were measured using a clonogenic long-term survival assay. Of these derivatives, 3-(...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.07.037

    authors： Shin SY,Ahn S,Yoon H,Jung H,Jung Y,Koh D,Lee YH,Lim Y

    更新日期：2016-09-01 00:00:00

  • Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity.

    abstract：:In order to define the structural requirements of quinazoline-2(1H)-thiones 1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1H)-thiones (3a-h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of alpha-MSH. The anti-...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.06.123

    authors： Thanigaimalai P,Sharma VK,Lee KC,Yun CY,Kim Y,Jung SH

    更新日期：2010-08-15 00:00:00

  • 2-Anilino-4-aryl-1,3-thiazole inhibitors of valosin-containing protein (VCP or p97).

    abstract：:Valosin-containing protein (VCP; also known as p97) is a member of the AAA ATPase family with a central role in the ubiquitin-degradation of misfolded proteins. VCP also exhibits antiapoptotic function and metastasis via activation of nuclear factor kappa-B signaling pathway. We have discovered that 2-anilino-4-aryl-1...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.01.058

    authors： Bursavich MG,Parker DP,Willardsen JA,Gao ZH,Davis T,Ostanin K,Robinson R,Peterson A,Cimbora DM,Zhu JF,Richards B

    更新日期：2010-03-01 00:00:00

  • Inhibition of carbonic anhydrase isozymes I, II and IX with benzenesulfonamides containing an organometallic moiety.

    abstract：:A novel series of benzenesulfonamides that contain ferrocenyl or ruthenocenyl moieties were synthesized and investigated for their ability to inhibit the enzymatic activity of physiologically relevant carbonic anhydrase (CA) isozymes: hCA I, II and tumour-associated IX (h=human). This manuscript describes the regiosel...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.07.024

    authors： Salmon AJ,Williams ML,Innocenti A,Vullo D,Supuran CT,Poulsen SA

    更新日期：2007-09-15 00:00:00

  • 5-Carboxamido-1,3,2-dioxaphosphorinanes, potent inhibitors of MTP.

    abstract：:5-Carboxamido-1,3,2-dioxaphosphorinanes have been identified as potent inhibitors of microsomal triglyceride-transfer protein. The 1,3,2-dioxaphosphorine functionality acted as a neutral and stable replacement for piperidine and piperidine N-oxide. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.07.069

    authors： Sulsky R,Robl JA,Biller SA,Harrity TW,Wetterau J,Connolly F,Jolibois K,Kunselman L

    更新日期：2004-10-18 00:00:00

  • Discovery of 4-substituted-8-(2-hydroxy-2-phenyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1-one as a novel class of highly selective GlyT1 inhibitors with improved metabolic stability.

    abstract：:A novel class of 4-aryl-8-(2-hydroxy-2-phenyl-cyclohexyl)-2,8-diaza-spiro[4.5]decan-1- ones have been discovered and developed as potent and selective GlyT1 inhibitors. The molecules are devoid of activity at the GlyT2 isoform and display excellent selectivities against the mu-opioid receptor as well as the Nociceptin...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.05.058

    authors： Alberati D,Hainzl D,Jolidon S,Krafft EA,Kurt A,Maier A,Pinard E,Thomas AW,Zimmerli D

    更新日期：2006-08-15 00:00:00

  • Proapoptotic modification of substituted isoindolinones as MDM2-p53 inhibitors.

    abstract：:A series of novel amino acid ester derivatives of 2,3-substituted isoindolinones was synthesized and evaluated for p53-mediated apoptotic activity. The rationale for augmentation of the target activity of 2,3-substituted isoindolinones was based on the introduction of new fragments in the structure of the inhibitor th...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.10.049

    authors： Grigoreva TA,Novikova DS,Petukhov AV,Gureev MA,Garabadzhiu AV,Melino G,Barlev NA,Tribulovich VG

    更新日期：2017-12-01 00:00:00

  • Modulating the development of E. coli biofilms with 2-aminoimidazoles.

    abstract：:The synthesis of a 20 member 2-aminoimidazole/triazole pilot library is reported. Each member of the library was screened for its ability to inhibit or promote biofilm development of either Escherichia coli and Acinetobacter baumannii. From this screen, E. coli-selective 2-aminoimidazoles were discovered, with the bes...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.08.075

    authors： Reed CS,Huigens RW 3rd,Rogers SA,Melander C

    更新日期：2010-11-01 00:00:00

  • Synthesis and biological evaluation of a new class of vaccine adjuvants: aminoalkyl glucosaminide 4-phosphates (AGPs).

    abstract：:A novel series of acylated omega-aminoalkyl 2-amino-2-deoxy-4-phosphono-beta-D-glucopyranosides (aminoalkyl glucosaminide 4-phosphates) was synthesized and screened for immunostimulant activity. Several of these compounds enhance the production of tetanus toxoid-specific antibodies in mice and augment vaccine-induced ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00374-1

    authors： Johnson DA,Sowell CG,Johnson CL,Livesay MT,Keegan DS,Rhodes MJ,Ulrich JT,Ward JR,Cantrell JL,Brookshire VG

    更新日期：1999-08-02 00:00:00

  • Synthesis, iron binding and antimicrobial properties of hexadentate 3-hydroxypyridinones-terminated dendrimers.

    abstract：:Macromolecular chelators have potential applications in the medical area, for instance, in treatment of iron overload-related disorders and in the treatment of external infections. In this investigation, several novel iron(III)-selective hydroxypyridinone hexadentate-terminated first and second generation dendrimeric ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2018.05.058

    authors： Zhou T,Chen K,Kong LM,Liu MS,Ma YM,Xie YY,Hider RC

    更新日期：2018-08-01 00:00:00