Synthesis of some new S-alkylated derivatives of 5-mercapto-2'-deoxyuridine as potential antiviral agents.

Abstract:

:A series of S-alkylated derivatives of 5-mercapto-2'-deoxyuridine have been prepared by alkylation of the preformed nucleoside. Two of these compounds, the S-propargyl and S-allyl derivatives, have shown significant antiviral activity against Herpes simplex type 1 in HeLa TK- cells but appear to be less effective in this assay system than some previously reported 5-substituted 2'-deoxyuridines.

journal_name

J Med Chem

authors

Dinan FJ,Bardos TJ

doi

10.1021/jm00179a019

subject

Has Abstract

pub_date

1980-05-01 00:00:00

pages

569-72

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

23

pub_type

杂志文章
  • N-benzoylated phenoxazines and phenothiazines: synthesis, antiproliferative activity, and inhibition of tubulin polymerization.

    abstract::A total of 53 N-benzoylated phenoxazines and phenothiazines, including their S-oxidized analogues, were synthesized and evaluated for antiproliferative activity, interaction with tubulin, and cell cycle effects. Potent inhibitors of multiple cancer cell lines emerged with the 10-(4-methoxybenzoyl)-10H-phenoxazine-3-ca...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm200436t

    authors: Prinz H,Chamasmani B,Vogel K,Böhm KJ,Aicher B,Gerlach M,Günther EG,Amon P,Ivanov I,Müller K

    更新日期:2011-06-23 00:00:00

  • Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists.

    abstract::The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm050879z

    authors: Raitio KH,Savinainen JR,Vepsäläinen J,Laitinen JT,Poso A,Järvinen T,Nevalainen T

    更新日期:2006-03-23 00:00:00

  • Nucleoside 5'-monophosphate analogues. Synthesis of 5'-sulfamino-5'-deoxynucleosides.

    abstract::The synthesis of two new nucleotide analogues is described. 5'-Sulfamino-5'-deoxyadenosine (1) was prepared by reaction of 5'-amino-5'-deoxyadenosine with (CH3)3N.203, and 5'-sulfamino-5'-deoxythymidine (2) was prepared from 5'-amino-5'-deoxythymidine by a similar reaction. The 5'-sulfamino nucleosides are shown to be...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00205a024

    authors: Mungall WS,Lemmen LJ,Lemmen KL,Dethmers JK,Norling LL

    更新日期:1978-07-01 00:00:00

  • Fragment Molecular Orbital Method Applied to Lead Optimization of Novel Interleukin-2 Inducible T-Cell Kinase (ITK) Inhibitors.

    abstract::Inhibition of inducible T-cell kinase (ITK), a nonreceptor tyrosine kinase, may represent a novel treatment for allergic asthma. In our previous reports, we described the discovery of sulfonylpyridine (SAP), benzothiazole (BZT), indazole (IND), and tetrahydroindazole (THI) series as novel ITK inhibitors and how comput...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/acs.jmedchem.6b00045

    authors: Heifetz A,Trani G,Aldeghi M,MacKinnon CH,McEwan PA,Brookfield FA,Chudyk EI,Bodkin M,Pei Z,Burch JD,Ortwine DF

    更新日期:2016-05-12 00:00:00

  • Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.

    abstract::(3-Phenyl-7-flavonoxy)propanolamines have been shown to exhibit antihypertensive activity in spontaneously hypertensive rats. Although they are structurally similar to classical beta-adrenergic blocking compounds, their activity is not due to inhibition of beta-adrenoceptors. In the present study, a series of simple f...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00121a034

    authors: Wu ES,Cole TE,Davidson TA,Dailey MA,Doring KG,Fedorchuk M,Loch JT 3rd,Thomas TL,Blosser JC,Borrelli AR

    更新日期:1989-01-01 00:00:00

  • Synthesis and structure-activity relationships of the novel homopropargylamine antimycotics.

    abstract::Analogues of the antimycotic allylamine terbinafine were prepared in which the naphthalene and the tert-butyl-acetylene moieties were preserved, but the spacer between these two groups was varied, and the antifungal activity of the new compounds was evaluated. All modifications of the original spacer such as reduction...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00031a010

    authors: Nussbaumer P,Leitner I,Stütz A

    更新日期:1994-03-04 00:00:00

  • Simple selection criteria for drug-like chemical matter.

    abstract::A simple pharmacophore point filter has been developed that discriminates between drug-like and nondrug-like chemical matter. It is based on the observation that nondrugs are often underfunctionalized. Therefore, a minimum count of well-defined pharmacophore points is required to pass the filter. The application of th...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm015507e

    authors: Muegge I,Heald SL,Brittelli D

    更新日期:2001-06-07 00:00:00

  • The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors.

    abstract::Coumarins constitute a general and totally new class of inhibitors of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), binding at the entrance of the active site cavity. We report here that the coumarin-binding site in CAs may interact with diverse compounds, such as the antiepileptic drug lacosamide, which inhibi...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm901524f

    authors: Temperini C,Innocenti A,Scozzafava A,Parkkila S,Supuran CT

    更新日期:2010-01-28 00:00:00

  • Further studies on the Dmt-Tic pharmacophore: hydrophobic substituents at the C-terminus endow delta antagonists to manifest mu agonism or mu antagonism.

    abstract::Twenty N- and/or C-modified Dmt-Tic analogues yielded similar K(i) values with either [(3)H]DPDPE (delta(1) agonist) or [(3)H]N, N(Me)(2)-Dmt-Tic-OH (delta antagonist). N-Methylation enhanced delta antagonism while N-piperidine-1-yl, N-pyrrolidine-1-yl, and N-pyrrole-1-yl were detrimental. Dmt-Tic-X (X = -NHNH(2), -NH...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm990165m

    authors: Salvadori S,Guerrini R,Balboni G,Bianchi C,Bryant SD,Cooper PS,Lazarus LH

    更新日期:1999-12-02 00:00:00

  • Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro-pentofuranosyl nucleosides.

    abstract::Following the recent discoveries that some L-nucleosides are more or equal potent than their D-counterparts, we synthesized 2'-deoxy-2',2'-difluoro-L-erythro-pentofuranosyl nucleosides as potential antiviral agents. The target compounds were synthesized via the key intermediates 7a or 7b from L-gulono gamma-lactone. C...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm970275y

    authors: Kotra LP,Xiang Y,Newton MG,Schinazi RF,Cheng YC,Chu CK

    更新日期:1997-10-24 00:00:00

  • Peripheral and axial substitution of phthalocyanines with solketal groups: synthesis and in vitro evaluation for photodynamic therapy.

    abstract::Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol)8 and Si(sol)2Pc, respectively, ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm061136w

    authors: Hofman JW,van Zeeland F,Turker S,Talsma H,Lambrechts SA,Sakharov DV,Hennink WE,van Nostrum CF

    更新日期:2007-04-05 00:00:00

  • Synthesis and biological evaluation of novel sigma-1 receptor antagonists based on pyrimidine scaffold as agents for treating neuropathic pain.

    abstract::The discovery and synthesis of a new series of pyrimidines as potent sigma-1 receptor (σ1R) antagonists, associated with pharmacological antineuropathic pain activity, are the focus of this article. The new compounds were evaluated in vitro in σ-1 and σ-2 receptor binding assays. The nature of the pyrimidine scaffold ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm501207r

    authors: Lan Y,Chen Y,Cao X,Zhang J,Wang J,Xu X,Qiu Y,Zhang T,Liu X,Liu BF,Zhang G

    更新日期:2014-12-26 00:00:00

  • Synthesis and biological evaluation of some cyclic phosphoramidate nucleoside derivatives.

    abstract::(E)-5-(2-Bromovinyl)-2'-deoxy-5'-O-(3-methyl-2-oxo-5-formyl-1,3,2- oxazaphosphacyclopentan-2-yl)uridine has been synthesized and, under physiological conditions and without the necessity for enzyme activity, has been shown to yield the 5'-nucleotide in vitro. Unfortunately this compound is not sufficiently stable in s...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00171a009

    authors: Kumar A,Coe PL,Jones AS,Walker RT,Balzarini J,De Clercq E

    更新日期:1990-09-01 00:00:00

  • Design and syntheses of 1,6-naphthalene derivatives as selective HCMV protease inhibitors.

    abstract::Through high throughput screening of various libraries, substituted styryl naphthalene 6 was identified as an HCMV protease inhibitor. Optimization of various regions of the lead molecule using parallel synthesis resulted in 1,6-substituted naphthalenes 19d-i. These compounds displayed good potency and were selective ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm030540h

    authors: Gopalsamy A,Lim K,Ellingboe JW,Mitsner B,Nikitenko A,Upeslacis J,Mansour TS,Olson MW,Bebernitz GA,Grinberg D,Feld B,Moy FJ,O'Connell J

    更新日期:2004-04-08 00:00:00

  • Synthesis of 2-(p-chlorobenzyl)-3-aryl-6-methoxybenzofurans as selective ligands for antiestrogen-binding sites. Effects on cell proliferation and cholesterol synthesis.

    abstract::A series of nonsteroidal compounds, 2-(p-chlorobenzyl)-3-aryl-6- methoxybenzofurans derived from the 2-(p-chlorobenzyl)-6-methoxy-3(2H)-benzofuranones has been synthesized. The key steps in the synthesis were reactions of 2-(p-chlorobenzyl)-6-methoxy-3(2H)-benzofuranones with the arylorganometallic reagents followed b...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00086a002

    authors: Teo CC,Kon OL,Sim KY,Ng SC

    更新日期:1992-04-17 00:00:00

  • 2-Phenylpyrroles as conformationally restricted benzamide analogues. A new class of potential antipsychotics. 1.

    abstract::2-Phenylpyrroles were synthesized as conformationally restricted analogues of the substituted benzamide sultopride and the butyrophenones haloperidol and fluanisone. Dopamine antagonistic activity is maintained if the 2-phenylpyrrole side chain is linked to the pharmacophoric N-ethylpyrrolidine moiety of sultopride or...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00394a028

    authors: van Wijngaarden I,Kruse CG,van Hes R,van der Heyden JA,Tulp MT

    更新日期:1987-11-01 00:00:00

  • High-affinity, non-nucleotide-derived competitive antagonists of platelet P2Y12 receptors.

    abstract::Anthraquinone derivatives related to the moderately potent, nonselective P2Y(12) receptor antagonist reactive blue 2 (6) have been synthesized and optimized with respect to P2Y(12) receptor affinity. A radioligand binding assay utilizing human blood platelet membranes and the P2Y(12) receptor-selective antagonist radi...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm9003297

    authors: Baqi Y,Atzler K,Köse M,Glänzel M,Müller CE

    更新日期:2009-06-25 00:00:00

  • Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics.

    abstract::Recently we have described the antitumor activities of 2-benzoxazolylhydrazones derived from 2-formyl and 2-acetylpyridines. In search of a more efficacious analogue, compounds in which the 2-acetylpyridine moiety has been replaced by 2-acylpyridine and alpha-(N)-acetyldiazine/quinoline groups have been synthesized. T...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm060232u

    authors: Easmon J,Pürstinger G,Thies KS,Heinisch G,Hofmann J

    更新日期:2006-10-19 00:00:00

  • cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.

    abstract::Novel, lipophilic cycloSal triesters 4a-c and 5a-c were synthesized, respectively, from the ara- and ribo-configurated 2'-fluorinated-2', 3'-dideoxyadenosines 2 and 3. The cycloSal phosphotriesters were used as tools to study the effects of the two different sugar pucker conformations induced by two opposite configura...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm981097r

    authors: Meier C,Knispel T,Marquez VE,Siddiqui MA,De Clercq E,Balzarini J

    更新日期:1999-05-06 00:00:00

  • Structure-activity relationship study of opiorphin, a human dual ectopeptidase inhibitor with antinociceptive properties.

    abstract::Toward developing new potential analgesics, this first structure-activity relationship study of opiorphin (H-Gln-Arg-Phe-Ser-Arg-OH), a human peptide inhibiting enkephalin degradation, was performed. A systematic Ala scanning proved that Phe(3) is a key residue for neprilysin and aminopeptidase N (AP-N) ectoenkephalin...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm2012112

    authors: Rosa M,Arsequell G,Rougeot C,Calle LP,Marcelo F,Pinto M,Centeno NB,Jiménez-Barbero J,Valencia G

    更新日期:2012-02-09 00:00:00

  • Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-bip

    abstract::Substitution at the ortho position of N-(3,4-dimethyl-5-isoxazolyl) benzenesulfonamide led to the identification of the biphenylsulfonamides as a novel series of endothelin-A (ETA) selective antagonists. Appropriate substitutions on the pendant phenyl ring led to improved binding as well as functional activity. A hydr...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm970872k

    authors: Murugesan N,Gu Z,Stein PD,Bisaha S,Spergel S,Girotra R,Lee VG,Lloyd J,Misra RN,Schmidt J,Mathur A,Stratton L,Kelly YF,Bird E,Waldron T,Liu EC,Zhang R,Lee H,Serafino R,Abboa-Offei B,Mathers P,Giancarli M,Seymou

    更新日期:1998-12-17 00:00:00

  • Synthesis and biological activity of camel and bovine beta-melanotropins.

    abstract::Two natural occurring melanotropins, camel betaC2-MSH and bovine beta-MSH, have been synthesized by improved solid-phase procedures. The coupling reaction of tert-butyloxycarbonylamino acids was achieved by using their preformed symmetrical anhydrides. The synthetic hormones were purified by gel filtration on Sephadex...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00225a006

    authors: Lemaire S,Yamashiro D,Li CH

    更新日期:1976-03-01 00:00:00

  • Synthesis and biological activities of novel pleuromutilin derivatives with a substituted thiadiazole moiety as potent drug-resistant bacteria inhibitors.

    abstract::A series of novel pleuromutilin derivatives possessing thiadiazole moieties were synthesized via acylation reactions under mild conditions. The in vitro antibacterial activities of the derivatives against methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Escherichia coli, a...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm500374c

    authors: Shang R,Pu X,Xu X,Xin Z,Zhang C,Guo W,Liu Y,Liang J

    更新日期:2014-07-10 00:00:00

  • Synthesis, in vivo occupancy, and radiolabeling of potent phosphodiesterase subtype-10 inhibitors as candidates for positron emission tomography imaging.

    abstract::We have recently reported the phosphodiesterase 10A (PDE10A) inhibitor 2-[4-[1-(2-[(18)F]fluoroethyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]-phenoxymethyl]-quinoline ([(18)F]1a) as a promising candidate for in vivo imaging using positron emission tomography (PET). We now describe the synthesis and biological evaluation of a ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm200536d

    authors: Andrés JI,De Angelis M,Alcázar J,Iturrino L,Langlois X,Dedeurwaerdere S,Lenaerts I,Vanhoof G,Celen S,Bormans G

    更新日期:2011-08-25 00:00:00

  • Challenges in the Discovery of Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors.

    abstract::Since the discovery of indoleamine 2,3-dioxygenase 1 (IDO1) as an attractive target for anticancer therapy in 2003, the search for inhibitors has been intensely pursued both in academia and in pharmaceutical companies. Many novel IDO1 inhibitor scaffolds have been described, and a few potent compounds have entered cli...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1021/acs.jmedchem.5b00326

    authors: Röhrig UF,Majjigapu SR,Vogel P,Zoete V,Michielin O

    更新日期:2015-12-24 00:00:00

  • Synthesis, conformation, and immunosuppressive activities of three analogues of cyclosporin A modified in the 1-position.

    abstract::The syntheses of three new cyclosporin A (CsA) analogues that contain novel MeBmt derivatives in the 1-position are described. The MeBmt analogue that contains an additional methyl group on C4, (2S,3R,6E)-4,4-dimethyl-3-hydroxy-2-(N-methylamino)-6-octenoic acid (MeBm2t), was synthesized in four steps beginning with th...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00165a018

    authors: Aebi JD,Deyo DT,Sun CQ,Guillaume D,Dunlap B,Rich DH

    更新日期:1990-03-01 00:00:00

  • Novel small molecule inhibitors of MDR Mycobacterium tuberculosis by NMR fragment screening of antigen 85C.

    abstract::Protein target-based discovery of novel antibiotics has been largely unsuccessful despite rich genome information. Particularly in need are new antibiotics for tuberculosis, which kills 1.6 million people annually and shows a rapid increase in multiple-drug-resistant cases. By combining fragment-based drug discovery w...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm100993z

    authors: Scheich C,Puetter V,Schade M

    更新日期:2010-12-09 00:00:00

  • Synthesis and structure-activity relationship of (lactamylvinyl)cephalosporins exhibiting activity against staphylococci, pneumococci, and enterococci.

    abstract::The synthesis and structure-activity relationships of a new class of vinylcephalosporins substituted with a lactamyl residue are described. These compounds show excellent activity against enterococci and retain the broad spectrum activity of third-generation cephalosporins such as ceftriaxone. ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm950886v

    authors: Heinze-Krauss I,Angehrn P,Guerry P,Hebeisen P,Hubschwerlen C,Kompis I,Page MG,Richter HG,Runtz V,Stalder H,Weiss U,Wei CC

    更新日期:1996-04-26 00:00:00

  • Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.

    abstract::A series of homo- and heterodimeric ligands containing kappa agonist and mu agonist/antagonist pharmacophores joined by a linker chain of varying lengths was synthesized and evaluated in vitro by their binding affinity at mu, delta, and kappa opioid receptors. The functional activities of these compounds were measured...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm050577x

    authors: Peng X,Knapp BI,Bidlack JM,Neumeyer JL

    更新日期:2006-01-12 00:00:00

  • Mono- or diphenylpyridazines connected to N-(2,4-difluorophenyl)-N'-heptylurea as acyl-CoA:cholesterol acyltransferase inhibitors.

    abstract::Mono- and diphenylpyridazine ureido derivatives, structurally related to DuP 128, were synthesized and tested for their inhibitory activity against ACAT isolated from rat liver microsomes. Several compounds displayed ACAT inhibition in the micromolar range. The amino derivatives 4a-c were also tested against hACAT-1 a...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm050703x

    authors: Gelain A,Bettinelli I,Barlocco D,Kwon BM,Jeong TS,Cho KH,Toma L

    更新日期:2005-12-01 00:00:00