Reactions of chloride salts of 7-amino-9-ethylguanine and 1-amino-3-methylbenzimidazoles with lead(IV) acetate: formation of 8-aza-9-ethylguanine and 1-methyl-1H-benzotriazoles.

Abstract:

:Reaction of 7-amino-9-ethylguaninium chloride with lead(IV) acetate (LTA) in MeOH yielded 8-aza-9-ethylguanine. Similarly, the reaction of 1-amino-3-methylbenzimidazolium chloride or its substituted derivatives (6-methyl, 5,6-dimethyl and 5-nitro) with LTA gave the corresponding 1-methyl-1H-benzotriazole (or 1-methyl-2-azabenzimidazole) derivatives along with N-methylformananilide derivatives.

journal_name

Bioorg Med Chem Lett

authors

Kaiya T,Aoyama S,Kohda K

doi

10.1016/s0960-894x(99)00123-7

subject

Has Abstract

pub_date

1999-04-05 00:00:00

pages

961-4

issue

7

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(99)00123-7

journal_volume

9

pub_type

杂志文章
  • Amino acids and peptides. Part 39: a bivalent poly(ethylene glycol) hybrid containing an active site (RGD) and its synergistic site (PHSRN) of fibronectin.

    abstract::Fibronectin contains the active sequence Arg-Gly-Asp (RGD), along with its synergic site Pro-His-Ser-Arg-Asn (PHSRN). However, the PHSRN peptide does not show synergic activity when it is mixed with the RGD peptide, indicating that a spatial array between RGD and PHSRN in fibronectin may be necessary for synergic acti...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00225-6

    authors: Hojo K,Susuki Y,Maeda M,Okazaki I,Nomizu M,Kamada H,Yamamoto Y,Nakagawa S,Mayumi T,Kawasaki K

    更新日期:2001-06-04 00:00:00

  • 2-Phenylbenzofuran derivatives alleviate mitochondrial damage via the inhibition of β-amyloid aggregation.

    abstract::To obtain modulators for reducing mitochondrial damage by the inhibition of Aβ oligomer formation, 2-phenylbenzofuran derivatives were designed and prepared. Their inhibitory activity against Aβ fibril formation was screened using ThT fluorescence assay, and the effect of derivatives on mitochondrial function was eval...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.08.087

    authors: Lee YS,Kim HY,Youn HM,Seo JH,Kim Y,Shin KJ

    更新日期:2013-11-01 00:00:00

  • Potent antiprotozoal activity of a novel semi-synthetic berberine derivative.

    abstract::Treatment of diseases such as African sleeping sickness and leishmaniasis often depends on relatively expensive or toxic drugs, and resistance to current chemotherapeutics is an issue in treating these diseases and malaria. In this study, a new semi-synthetic berberine analogue, 5,6-didehydro-8,8-diethyl-13-oxodihydro...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.01.101

    authors: Bahar M,Deng Y,Zhu X,He S,Pandharkar T,Drew ME,Navarro-Vázquez A,Anklin C,Gil RR,Doskotch RW,Werbovetz KA,Kinghorn AD

    更新日期:2011-05-01 00:00:00

  • Synthesis of Vorinostat and cholesterol conjugate to enhance the cancer cell uptake selectivity.

    abstract::Histone deacetylase (HDAC) inhibitors modulate various cellular functions including proliferation, differentiation, and apoptosis. Vorinostat (SuberAniloHydroxamic Acid, SAHA) is the first HDAC inhibitor approved by FDA for cancer treatment. However, SAHA distributes in cancer tissue and normal tissue in similar level...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.01.025

    authors: Idippily ND,Gan C,Orefice P,Peterson J,Su B

    更新日期:2017-02-15 00:00:00

  • High affinity sialoside ligands of myelin associated glycoprotein.

    abstract::Myelin associated glycoprotein (Siglec-4) is a myelin adhesion receptor, that is, well established for its role as an inhibitor of axonal outgrowth in nerve injury, mediated by binding to sialic acid containing ligands on the axonal membrane. Because disruption of myelin-ligand interactions promotes axon outgrowth, we...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.04.068

    authors: Zeng Y,Rademacher C,Nycholat CM,Futakawa S,Lemme K,Ernst B,Paulson JC

    更新日期:2011-09-01 00:00:00

  • Design and synthesis of novel substituted quinazoline derivatives as antileishmanial agents.

    abstract::4-(Substituted-benzylidine)-2-substituted-5,6-dihydrobenzo[h]quinazoline (5a-p) and 4-(substituted-benzylidine)-2-substituted-3, 4, 5, 6-tetrahydrobenzo[h]quinazoline (6a-p) have been synthesized from 2-(substituted-benzylidine)tetralone-1(3a-d) and several substituted guanidine sulfates(4a-d).These compounds were tes...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.07.081

    authors: Agarwal KC,Sharma V,Shakya N,Gupta S

    更新日期:2009-09-15 00:00:00

  • Novel targeting strategy based on multimeric ligands for drug delivery and molecular imaging: homooligomers of alpha-MSH.

    abstract::Homooligomers constructed with 4- and 6-amino acid fragments of melanocortin (alpha-MSH) bind with higher affinity and with apparent cooperativity to melanocortin receptor, compared to their constituent monomers. Individual ligands were tethered with various spacers of different length and rigidity and the influence o...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.09.079

    authors: Vagner J,Handl HL,Gillies RJ,Hruby VJ

    更新日期:2004-01-05 00:00:00

  • Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir.

    abstract::A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00329-3

    authors: Honda T,Masuda T,Yoshida S,Arai M,Kaneko S,Yamashita M

    更新日期:2002-08-05 00:00:00

  • Effects of positional and geometrical isomerism on the biological activity of some novel oxazolidinones.

    abstract::Some novel oxazolidinone derivatives with benzotriazole as pendant have been synthesized and tested for antibacterial activity. Linearly attached benzotriazole derivative showed more potency compared to angular one in vitro. Out of E/Z-isomers of angularly attached derivatives E-isomer was found to be more potent than...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.10.073

    authors: Das J,Rao CV,Sastry TV,Roshaiah M,Sankar PG,Khadeer A,Kumar MS,Mallik A,Selvakumar N,Iqbal J,Trehan S

    更新日期:2005-01-17 00:00:00

  • Alpha-keto amides as inhibitors of histone deacetylase.

    abstract::Alpha-keto ester and amides were found to be potent inhibitors of histone deacetylase. Nanomolar inhibitors against the isolated enzyme and sub-micromolar inhibitors of cellular proliferation were obtained. The alpha-keto amide 30 also exhibited significant anti-tumor effects in an in vivo tumor model. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00685-1

    authors: Wada CK,Frey RR,Ji Z,Curtin ML,Garland RB,Holms JH,Li J,Pease LJ,Guo J,Glaser KB,Marcotte PA,Richardson PL,Murphy SS,Bouska JJ,Tapang P,Magoc TJ,Albert DH,Davidsen SK,Michaelides MR

    更新日期:2003-10-06 00:00:00

  • Rapid 'one-pot' synthesis of a novel benzimidazole-5-carboxylate and its hydrazone derivatives as potential anti-inflammatory and antimicrobial agents.

    abstract::A novel series of N-arylidene-2-(2,4-dichloro phenyl)-1-propyl-1H-benzo[d] imidazole-5-carbohydrazides having different substitution on the arylidene part were synthesized in good yield. The core nucleus benzimidazole-5-carboxylate (5) was efficiently synthesized by 'one-pot' nitro reductive cyclization reaction betwe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.02.043

    authors: Vasantha K,Basavarajaswamy G,Vaishali Rai M,Boja P,Pai VR,Shruthi N,Bhat M

    更新日期:2015-04-01 00:00:00

  • Surface plasmon resonance-based detection of ladder-shaped polyethers by inhibition detection method.

    abstract::Ladder-shaped polyether (LSP) compounds represented by brevetoxins and ciguatoxins were largely discovered in association with seafood poisoning. Thus, a quick quantification method for LSPs is potentially important. We examined a surface plasmon resonance method using desulfated-yessotoxin (dsYTX) immobilized on a se...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.03.103

    authors: Mouri R,Oishi T,Torikai K,Ujihara S,Matsumori N,Murata M,Oshima Y

    更新日期:2009-05-15 00:00:00

  • 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARalpha/gamma agonists. Part I: synthesis and pharmacological evaluation.

    abstract::Type-2 diabetes (T2D) is a complex metabolic disease characterized by insulin resistance in the liver and peripheral tissues accompanied by a defect in pancreatic beta-cell. Since their discovery three subtypes of Peroxisomes Proliferators Activated Receptors were identified namely PPARalpha, PPARgamma and PPARbeta/(d...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.01.067

    authors: Parmenon C,Guillard J,Caignard DH,Hennuyer N,Staels B,Audinot-Bouchez V,Boutin JA,Dacquet C,Ktorza A,Viaud-Massuard MC

    更新日期:2008-03-01 00:00:00

  • Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives.

    abstract::The Naturally occurring novel cyclohexanonyl bromophenol 2(R)-2-(2,3,6-tribromo-4,5-dihydroxybenzyl)cyclohexanone (4) was synthesized as a racemic compound. Cyclohexylphenyl methane derivatives (10-17) with Br, OMe, CO, and OH were also obtained. Inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.12.069

    authors: Balaydın HT,Sentürk M,Menzek A

    更新日期:2012-02-01 00:00:00

  • Highly sensitive and selective detection of Al(III) ions in aqueous buffered solution with fluorescent peptide-based sensor.

    abstract::A fluorescent sensor based on a tripeptide (SerGluGlu) with a dansyl fluorophore detected selectively Al(III) among 16 metal ions in aqueous buffered solutions without any organic cosolvent. The peptide-based sensor showed a highly sensitive turn on response to aluminium ion with high binding affinity (1.84×10(4)M(-1)...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.07.073

    authors: In B,Hwang GW,Lee KH

    更新日期:2016-09-15 00:00:00

  • Substituted aminobenzimidazole pyrimidines as cyclin-dependent kinase inhibitors.

    abstract::A series of aminobenzimidazole-substituted pyrimidines were synthesized and evaluated for biochemical activity against CDK1. A high-speed parallel synthesis approach enabled the identification of a potent lead series having improved potency in the CDK1 assay (IC(50)<10nM). Cell cycle analysis showed that the compounds...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.02.076

    authors: Verma S,Nagarathnam D,Shao J,Zhang L,Zhao J,Wang Y,Li T,Mull E,Enyedy I,Wang C,Zhu Q,Altieri M,Jordan J,Dang TT,Reddy S

    更新日期:2005-04-15 00:00:00

  • Identification of Darmstoff analogs as selective agonists and antagonists of lysophosphatidic acid receptors.

    abstract::Darmstoff describes a family of gut smooth muscle-stimulating acetal phosphatidic acids initially isolated and characterized from the bath fluid of stimulated gut over 50 years ago. Despite similar structural and biological profiles, Darmstoff analogs have not previously been examined as potential LPA mimetics. Here, ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.08.096

    authors: Gududuru V,Zeng K,Tsukahara R,Makarova N,Fujiwara Y,Pigg KR,Baker DL,Tigyi G,Miller DD

    更新日期:2006-01-15 00:00:00

  • Dinucleotide cap analogue affinity resins for purification of proteins that specifically recognize the 5' end of mRNA.

    abstract::Here we present first dinucleotide affinity resins for purification of proteins that specifically recognize the 5' end of mRNA. Constructed resins possess either a naturally occurring mono- or trimethylated cap or their analogues resistant towards enzymatic degradation, bearing a CH(2) bridge between β and γ position ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.08.026

    authors: Jankowska-Anyszka M,Piecyk K

    更新日期:2011-10-15 00:00:00

  • Interaction between morphine and lysine.

    abstract::The study by the molecular orbital theory displayed that morphine and lysine make two types of the interactions between them: type (A) by three hydrogen bondings and type (B) by one hydrogen bonding accompanied with a proton transfer. The stabilization energies were 45.3 and 34.9 kcal/mol for type (A) and type (B), re...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00228-1

    authors: Nakai S,Yoneda F

    更新日期:2001-06-04 00:00:00

  • Anticonvulsant and analgesic in neuropathic pain activity in a group of new aminoalkanol derivatives.

    abstract::As part of the presented research, thirteen new aminoalkanol derivatives were designed and obtained by chemical synthesis. In vivo studies (mice, i.p.) showed anticonvulsant activity (MES) of nine compounds, and in the case of one compound (R,S-trans-2-((2-(2,3,5-trimethylphenoxy)ethyl)amino)cyclohexan-1-ol, 4) both a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127325

    authors: Pańczyk K,Rapacz A,Furgała-Wojas A,Sałat K,Koczurkiewicz-Adamczyk P,Łucjanek M,Skiba-Kurek I,Karczewska E,Sowa A,Żelaszczyk D,Siwek A,Popiół J,Pękala E,Marona H,Waszkielewicz A

    更新日期:2020-08-15 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

  • Design and synthesis of 2-phenylpyrimidine coumarin derivatives as anticancer agents.

    abstract::A series of 2-phenylpyrimidine coumarin derivatives with potential telomerase-inhibiting activity was designed and synthesized. All of the compounds were screened for antiproliferative activity against CNE2, KB, and Cal27 cell lines in vitro. The results showed that most of the derivatives had a favorable effect on re...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.08.044

    authors: Lv N,Sun M,Liu C,Li J

    更新日期:2017-10-01 00:00:00

  • Development of novel tail-modified anandamide analogs.

    abstract::To explore the hydrophobic groove subsite within the CB1 cannabinoid receptor we have designed and synthesized a group of tail-substituted anandamide analogs. Our design involves the introduction of aryl or heterocyclic ring as terminal substituents that are connected to the last cis-arachidonyl double bond through al...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.07.110

    authors: Yao F,Li C,Vadivel SK,Bowman AL,Makriyannis A

    更新日期:2008-11-15 00:00:00

  • New insights into pradimicin biosynthesis revealed by two O-methyltransferases.

    abstract::Pradimicins are a group of antiviral and antifungal natural products from Actinomadura hibisca. Two putative O-methyltransferase genes, pdmF and pdmT, are present in the pradimicin biosynthetic gene cluster. However, there is only one methoxy group (11-OCH3) in pradimicins. Through heterologous expression and in vitro...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.05.068

    authors: Xu F,Napan K,Zhang S,Gladwin T,Takemoto J,Zhan J

    更新日期:2017-08-01 00:00:00

  • Syntheses and biological evaluation of ring-C modified colchicine analogs.

    abstract::Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels-Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through re...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.03.056

    authors: Yang B,Zhu ZC,Goodson HV,Miller MJ

    更新日期:2010-06-15 00:00:00

  • Benzo[7]annulene-based GluN2B selective NMDA receptor antagonists: Surprising effect of a nitro group in 2-position.

    abstract::Benzo[7]annulen-7-amines 7 without further polar substituents have been reported as conformationally restricted Ro 25-6981 analogs and show unexpectedly high GluN2B affinity. Herein the corresponding 2-NO2 derivatives 8 were synthesized and pharmacologically evaluated. NO2 derivatives 8 show 5- to 10-fold higher GluN2...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.10.076

    authors: Gawaskar S,Schepmann D,Bonifazi A,Robaa D,Sippl W,Wünsch B

    更新日期:2015-12-15 00:00:00

  • Rational design, synthesis and antitubercular evaluation of novel 2-(trifluoromethyl)phenothiazine-[1,2,3]triazole hybrids.

    abstract::Molecular hybridization is an emerging structural modification tool to design molecules with better pharmacophoric properties. A series of novel 2-(trifluoromethyl)phenothiazine-1,2,3-triazoles 5a-v designed by hybridizing two antitubercular drugs trifluoperazine and I-A09 in a single molecular architecture, were synt...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.11.031

    authors: Addla D,Jallapally A,Gurram D,Yogeeswari P,Sriram D,Kantevari S

    更新日期:2014-01-01 00:00:00

  • Novel bis-arylsulfonamides and aryl sulfonimides as inactivators of plasminogen activator inhibitor-1 (PAI-1).

    abstract::Inactivators of plasminogen activator inhibitor-1 (PAI-1) have been identified as possible treatments for a range of conditions, including atherosclerosis, venous thrombosis, and obesity. We describe the synthesis and inhibitory activity of a novel series of compounds based on bis-arylsulfonamide and aryl sulfonimide ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.12.051

    authors: El-Ayache NC,Li SH,Warnock M,Lawrence DA,Emal CD

    更新日期:2010-02-01 00:00:00

  • Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan.

    abstract::N-substituted chitosan and quaternized chitosan were synthesized and their antioxidant activity against hydroxyl radicals was assessed, respectively. Compared with the antioxidant activity of chitosan, the results indicated that the two kinds of chitosan derivatives had different scavenging ability on hydroxyl radical...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.09.009

    authors: Guo Z,Liu H,Chen X,Ji X,Li P

    更新日期:2006-12-15 00:00:00

  • Synthesis and cytotoxicity of (-)-renieramycin G analogs.

    abstract::(-)-Renieramycin G and fifteen C-22 analogs were prepared employing l-tyrosine as the chiral starting material. These analogs, along with (-)-renieramycin G itself, were evaluated in vitro for cytotoxicity against HCT-8, BEL-7402, A2780, MCF-7, A549, BGC-823, Ketr3, KB, Hela cells. The IC(50) values of most of these a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.01.025

    authors: Liu W,Dong W,Liao X,Yan Z,Guan B,Wang N,Liu Z

    更新日期:2011-03-01 00:00:00