当前位置： SCI文献检索 > JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Nitrogen-bridged conformationally constrained etorphine analogues. Synthesis and biological evaluation.

Nitrogen-bridged conformationally constrained etorphine analogues. Synthesis and biological evaluation.

Abstract：

:Three N-C8-bridged analogues 4-6 of the opiate etorphine (3) were synthesized and evaluated for opiate agonism and antagonism. In each case ring closure was effected by intramolecular N-alkylation with a suitably developed C8 side chain. Another key synthetic step was the selective monoprotection of diol 11, which allowed independent elaborations of the C7 and C8 side chains. All three analogues showed distinctly diminished agonist activities when compared to the corresponding N-methyl compound, 19(R)-n-butylorvinol (3). Furthermore, no antagonist activity was detectable. The results demonstrate that the conformation at the amino nitrogen in rigid morphinans is critical for potent opiate activity.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Maurer PJ,Rapoport H

doi

10.1021/jm00394a016

subject

Has Abstract

pub_date

1987-11-01 00:00:00

pages

2016-26

issue

11

eissn

0022-2623

issn

1520-4804

journal_volume

30

pub_type

杂志文章

相关文献

JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Optimization of brain penetrant 11β-hydroxysteroid dehydrogenase type I inhibitors and in vivo testing in diet-induced obese mice.

    abstract：:11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1) has been widely considered by the pharmaceutical industry as a target to treat metabolic syndrome in type II diabetics. We hypothesized that central nervous system (CNS) penetration might be required to see efficacy. Starting from a previously reported pyrimidine comp...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm4016729

    authors： Goldberg FW,Dossetter AG,Scott JS,Robb GR,Boyd S,Groombridge SD,Kemmitt PD,Sjögren T,Gutierrez PM,deSchoolmeester J,Swales JG,Turnbull AV,Wild MJ

    更新日期：2014-02-13 00:00:00

  • Cyclopentadienyl-ruthenium(II) and iron(II) organometallic compounds with carbohydrate derivative ligands as good colorectal anticancer agents.

    abstract：:New ruthenium(II) and iron(II) organometallic compounds of general formula [(η(5)-C5H5)M(PP)Lc][PF6], bearing carbohydrate derivative ligands (Lc), were prepared and fully characterized and the crystal structures of five of those compounds were determined by X-ray diffraction studies. Cell viability of colon cancer HC...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.5b00403

    authors： Florindo PR,Pereira DM,Borralho PM,Rodrigues CM,Piedade MF,Fernandes AC

    更新日期：2015-05-28 00:00:00

  • Identification of a new scaffold for opioid receptor antagonism based on the 2-amino-1,1-dimethyl-7-hydroxytetralin pharmacophore.

    abstract：:The trans-(3,4)-dimethyl-4-(3-hydroxyphenyl)piperidines are a unique class of opioid antagonists that have recently provided selective antagonists for mu-opioid receptors (MOR) and kappa-opioid receptors (KOR). Molecular modeling indicated a strong structural similarity between the parent of this series and 2-amino-1,...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm040807s

    authors： Grundt P,Williams IA,Lewis JW,Husbands SM

    更新日期：2004-10-07 00:00:00

  • Substituted imidazo[2,3-alpha]pyridine-2-carbamate anthelmintics.

    abstract：:Anthelmintic efficacies of a series of 6-substituted methyl imidazo[1,2-alpha]pyridine-2-carbamates were compared to similarly substituted benzimidazole-2-carbamates. With only one exception, methyl 6-benzoylimidazo[1,2-alpha]pyridine-2-carbamate, both classes of compounds exhibited similar activity vs. Nematospiroide...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00144a030

    authors： Bochis RJ,Olen LE,Waksmunski FS,Mrozik H,Eskola P,Kulsa P,Wilks G,Taylor JE,Egerton JR,Ostlind DA,Olson G

    更新日期：1981-12-01 00:00:00

  • Discovery of imidazo[1,2-b]thiazole derivatives as novel SIRT1 activators.

    abstract：:A series of imidazo[1,2-b]thiazole derivatives is shown to activate the NAD(+)-dependent deacetylase SIRT1, a potential new therapeutic target to treat various metabolic disorders. This series of compounds was derived from a high throughput screening hit bearing an oxazolopyridine core. Water-solubilizing groups could...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm8012954

    authors： Vu CB,Bemis JE,Disch JS,Ng PY,Nunes JJ,Milne JC,Carney DP,Lynch AV,Smith JJ,Lavu S,Lambert PD,Gagne DJ,Jirousek MR,Schenk S,Olefsky JM,Perni RB

    更新日期：2009-03-12 00:00:00

  • Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.

    abstract：:1, 8-Disubstituted derivatives of adenosine cyclic 3', 5'-phosphate (cAMP) were synthesized by N-oxidation or N-methylation of previously reported 8-substituted cAMP derivatives to yield 8-bromoadenosine cyclic 3', 5'-phosphate 1-oxide and 8-(benzylthio)-1-methyladenosine cyclic 3', 5'-phosphate. Substituents were int...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00225a017

    authors： Uno H,Meyer RB,Shuman DA,Robins RK,Simon LN,Miller JP

    更新日期：1976-03-01 00:00:00

  • Alkenylidene bisphenols, a new class of bisphenol bactericide.

    abstract：:Alkenylidene bisphenols are prepared by condensation of an appropriate phenol with a haloacetaldehyde, followed by base-induced elimination, or by condensation of the corresponding aryl methyl ether, elimination, and deprotection of the phenol with boron tribromide. The resulting compounds may be further elaborated by...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00194a022

    authors： Conradi RA,Vander Wyk JC,Bowlus SB

    更新日期：1979-08-01 00:00:00

  • Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma.

    abstract：:A novel class of 21-aminosteroids has been developed. Compounds within this series are potent inhibitors of iron-dependent lipid peroxidation in rat brain homogenates with IC50's as low as 3 microM. Furthermore, selected members enhance early neurological recovery and survival in a mouse head injury model. Significant...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00166a010

    authors： Jacobsen EJ,McCall JM,Ayer DE,Van Doornik FJ,Palmer JR,Belonga KL,Braughler JM,Hall ED,Houser DJ,Krook MA

    更新日期：1990-04-01 00:00:00

  • Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity.

    abstract：:The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1- n-octyl-1 H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-fused ring motif was affirmed...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.8b00777

    authors： Nyantakyi SA,Li M,Gopal P,Zimmerman M,Dartois V,Gengenbacher M,Dick T,Go ML

    更新日期：2018-07-12 00:00:00

  • Synthesis and carcinogenic activity of oxidized benzacridines: potential metabolites of the strong carcinogen 7-methylbenz[c]acridine and of the inactive isomer 12-methylbenz[a]acridine.

    abstract：:The synthesis of 15 compounds related either to the benz[c]acridine or to the benz[a]acridine series is reported. Spectral data, i.e., NMR and EI fragmentation, are given. These compounds were tested for carcinogenic activity in mice of the XVIInc/Z strain by subcutaneous injection. Only three weak carcinogens were de...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00356a038

    authors： Croisy-Delcey M,Croisy A,Zajdela F,Lhoste JM

    更新日期：1983-02-01 00:00:00

  • Activity of aromatic substituted phenylpiperazines lacking affinity for dopamine binding sites in a preclinical test of antipsychotic efficacy.

    abstract：:Generally, antipsychotic agents are dopamine receptor blocking agents that also block conditioned avoidance responding (CAR) in the rat. Recently, however, both (Q-methoxyphenyl)piperazine (OMPP, 1h) and (m-chlorophenyl)piperazine (MCPP, 1o) have been reported to block conditioned avoidance responding in the rat altho...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00125a020

    authors： Martin GE,Elgin RJ Jr,Mathiasen JR,Davis CB,Kesslick JM,Baldy WJ,Shank RP,DiStefano DL,Fedde CL,Scott MK

    更新日期：1989-05-01 00:00:00

  • The discovery and characterization of the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor potentiator N-{(3S,4S)-4-[4-(5-cyano-2-thienyl)phenoxy]tetrahydrofuran-3-yl}propane-2-sulfonamide (PF-04958242).

    abstract：:A unique tetrahydrofuran ether class of highly potent α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor potentiators has been identified using rational and structure-based drug design. An acyclic lead compound, containing an ether-linked isopropylsulfonamide and biphenyl group, was pharmacologically augmen...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.5b00300

    authors： Shaffer CL,Patel NC,Schwarz J,Scialis RJ,Wei Y,Hou XJ,Xie L,Karki K,Bryce DK,Osgood SM,Hoffmann WE,Lazzaro JT,Chang C,McGinnis DF,Lotarski SM,Liu J,Obach RS,Weber ML,Chen L,Zasadny KR,Seymour PA,Schmidt CJ,Haj

    更新日期：2015-05-28 00:00:00

  • Reversion of human Pgp-dependent multidrug resistance by new sesquiterpenes from Zinowiewia costaricensis.

    abstract：:In an intensive study of South American medicinal plants, herein we report the isolation, structure elucidation and biological activity of fourteen new and five known dihydro-beta-agarofuran sesquiterpenes from the leaves of Zinowiewia costaricensis (1-19). Their structures were determined by means of (1)H and (13)C N...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm058003f

    authors： Muñoz-Martínez F,Mendoza CR,Bazzocchi IL,Castanys S,Jiménez IA,Gamarro F

    更新日期：2005-06-30 00:00:00

  • Targeting zymogen activation to control the matriptase-prostasin proteolytic cascade.

    abstract：:Membrane-associated serine protease matriptase has been implicated in human diseases and might be a drug target. In the present study, a novel class of matriptase inhibitors targeting zymogen activation is developed by a combination of the screening of compound library using a cell-based matriptase activation assay an...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm200920s

    authors： Xu Z,Chen YW,Battu A,Wilder P,Weber D,Yu W,Mackerell AD,Chen LM,Chai KX,Johnson MD,Lin CY

    更新日期：2011-11-10 00:00:00

  • Discovery of (2S)-8-[(3R)-3-methylmorpholin-4-yl]-1-(3-methyl-2-oxobutyl)-2-(trifluoromethyl)-3,4-dihydro-2H-pyrimido[1,2-a]pyrimidin-6-one: a novel potent and selective inhibitor of Vps34 for the treatment of solid tumors.

    abstract：:Vps34 (the human class III phosphoinositide 3-kinase) is a lipid kinase involved in vesicle trafficking and autophagy and therefore constitutes an interesting target for cancer treatment. Because of the lack of specific Vps34 kinase inhibitors, we aimed to identify such compounds to further validate the role of this l...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm5013352

    authors： Pasquier B,El-Ahmad Y,Filoche-Rommé B,Dureuil C,Fassy F,Abecassis PY,Mathieu M,Bertrand T,Benard T,Barrière C,El Batti S,Letallec JP,Sonnefraud V,Brollo M,Delbarre L,Loyau V,Pilorge F,Bertin L,Richepin P,Arigon J,

    更新日期：2015-01-08 00:00:00

  • Design, synthesis, and binding affinities of potential positron emission tomography (PET) ligands for visualization of brain dopamine D3 receptors.

    abstract：:We here report the synthesis of compounds structurally related to the high-affinity dopamine D(3) receptor ligand N-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]-7-methoxy-2-benzofurancarboxamide (1). All compounds were specifically designed as potential PET radioligands for brain D(3) receptors visualization, havin...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm050734s

    authors： Leopoldo M,Lacivita E,De Giorgio P,Colabufo NA,Niso M,Berardi F,Perrone R

    更新日期：2006-01-12 00:00:00

  • Distamycin analogues with enhanced lipophilicity: synthesis and antimicrobial activity.

    abstract：:Forty-eight heterocyclic amino acid trimers, analogues of distamycin, with a number of features that enhance lipophilicity are described. They contain alkyl or cycloalkyl groups larger than methyl; some are N-terminated by acetamide or methoxybenzamide and are C-terminated by dimethylaminopropyl or aliphatic heterocyl...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm031089x

    authors： Khalaf AI,Waigh RD,Drummond AJ,Pringle B,McGroarty I,Skellern GG,Suckling CJ

    更新日期：2004-04-08 00:00:00

  • Design, synthesis, and dopamine receptor modulating activity of spiro bicyclic peptidomimetics of L-prolyl-L-leucyl-glycinamide.

    abstract：:In the present study, the synthesis of the 5.5.6. and 5.6.5. spiro bicyclic lactam PLG peptidomimetics, compounds 3 and 4, respectively, was undertaken. These peptidomimetics were designed to examine the following: (1) the effect that changing the size of the thiazolidine and lactam ring systems would have on the abil...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm980525q

    authors： Khalil EM,Ojala WH,Pradhan A,Nair VD,Gleason WB,Mishra RK,Johnson RL

    更新日期：1999-02-25 00:00:00

  • Optimization of cellular activity of G9a inhibitors 7-aminoalkoxy-quinazolines.

    abstract：:Protein lysine methyltransferase G9a plays key roles in the transcriptional repression of a variety of genes via dimethylation of lysine 9 on histone H3 (H3K9me2) of chromatin as well as dimethylation of nonhistone proteins including tumor suppressor p53. We previously reported the discovery of UNC0321 (3), the most p...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm200903z

    authors： Liu F,Barsyte-Lovejoy D,Allali-Hassani A,He Y,Herold JM,Chen X,Yates CM,Frye SV,Brown PJ,Huang J,Vedadi M,Arrowsmith CH,Jin J

    更新日期：2011-09-08 00:00:00

  • CYP53A15 of Cochliobolus lunatus, a target for natural antifungal compounds.

    abstract：:A novel cytochrome P450, CYP53A15, was identified in the pathogenic filamentous ascomycete Cochliobolus lunatus. The protein, classified into the CYP53 family, was capable of para hydroxylation of benzoate. Benzoate is a key intermediate in the metabolism of aromatic compounds in fungi and yet basically toxic to the o...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm800030e

    authors： Podobnik B,Stojan J,Lah L,Krasevec N,Seliskar M,Rizner TL,Rozman D,Komel R

    更新日期：2008-06-26 00:00:00

  • Discovery and optimization of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2: a structural basis for the reduction of albumin binding.

    abstract：:Methionine aminopeptidase-2 (MetAP2) is a novel target for cancer therapy. As part of an effort to discover orally active reversible inhibitors of MetAP2, a series of anthranilic acid sulfonamides with micromolar affinities for human MetAP2 were identified using affinity selection by mass spectrometry (ASMS) screening...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm0601001

    authors： Sheppard GS,Wang J,Kawai M,Fidanze SD,BaMaung NY,Erickson SA,Barnes DM,Tedrow JS,Kolaczkowski L,Vasudevan A,Park DC,Wang GT,Sanders WJ,Mantei RA,Palazzo F,Tucker-Garcia L,Lou P,Zhang Q,Park CH,Kim KH,Petros A,Ol

    更新日期：2006-06-29 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

  • Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives.

    abstract：:The synthesis of chiral 1,5-benzothiazepines 2a-c, 14a-c, 15c, and 16a prepared from cysteine is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound. Compound 2c was the most potent in vitro having an IC50 of 2.95 nM. The ester of 2c, i.e. 14c, was found to inhibit the A...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00148a024

    authors： Slade J,Stanton JL,Ben-David D,Mazzenga GC

    更新日期：1985-10-01 00:00:00

  • Novel, potent, and radio-iodinatable somatostatin receptor 1 (sst1) selective analogues.

    abstract：:The proposed sst(1) pharmacophore (J. Med. Chem. 2005, 48, 523-533) derived from the NMR structures of a family of mono- and dicyclic undecamers was used to design octa-, hepta-, and hexamers with high affinity and selectivity for the somatostatin sst(1) receptor. These compounds were tested for their in vitro binding...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm801314f

    authors： Erchegyi J,Cescato R,Grace CR,Waser B,Piccand V,Hoyer D,Riek R,Rivier JE,Reubi JC

    更新日期：2009-05-14 00:00:00

  • Drug Discovery Targeting Anaplastic Lymphoma Kinase (ALK).

    abstract：:As a receptor tyrosine kinase of insulin receptor (IR) subfamily, anaplastic lymphoma kinase (ALK) has been validated to play important roles in various cancers, especially anaplastic large cell lymphoma (ALCL), nonsmall cell lung cancer (NSCLC), and neuroblastomas. Currently, five small-molecule inhibitors of ALK, in...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1021/acs.jmedchem.9b00446

    authors： Kong X,Pan P,Sun H,Xia H,Wang X,Li Y,Hou T

    更新日期：2019-12-26 00:00:00

  • A novel approach for the development of selective Cdk4 inhibitors: library design based on locations of Cdk4 specific amino acid residues.

    abstract：:Identification of a selective inhibitor for a particular protein kinase without inhibition of other kinases is critical for use as a biological tool or drug. However, this is very difficult because there are hundreds of homologous kinases and their kinase domains including the ATP binding pocket have a common folding ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm010326y

    authors： Honma T,Yoshizumi T,Hashimoto N,Hayashi K,Kawanishi N,Fukasawa K,Takaki T,Ikeura C,Ikuta M,Suzuki-Takahashi I,Hayama T,Nishimura S,Morishima H

    更新日期：2001-12-20 00:00:00

  • Nitro and amino derivatives of lucanthone as antitumor agents.

    abstract：:A group of nitro and amino derivatives of lucanthone was prepared and tested for antitumor activity. Reaction of 1-chloro-4-methyl-7-nitrothioxanthenone and N,N-diethylethylenediamine gave the 7-amino analogue (11) directly, accompanied by 7-amino-1-chloro-4-methylthioxanthenone. The antitumor activity of 11 was infer...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00345a020

    authors： Archer S,Rej R

    更新日期：1982-03-01 00:00:00

  • Influence of conformation and intramolecular hydrogen bonding on the acyl glucuronidation and biliary excretion of acetylenic bis-dipyrrinones related to bilirubin.

    abstract：:Glucuronidation and transporter-mediated efflux into bile are important in the elimination of xeno- and endobiotics, including the natural biladienone pigment bilirubin. The mechanisms of these processes and the structural factors that dictate whether cholephilic compounds are excreted directly in bile or require prio...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm0609521

    authors： McDonagh AF,Lightner DA

    更新日期：2007-02-08 00:00:00

  • Synthesis and biological studies of different duocarmycin based glycosidic prodrugs for their use in the antibody-directed enzyme prodrug therapy.

    abstract：:The synthesis and biological evaluation of novel prodrugs for use in the antibody directed enzyme prodrug therapy (ADEPT) of cancer based on the cytotoxic antibiotic duocarmycin SA (1) are described. In this approach, we investigated the influence of the sugar moiety of the glycosidic prodrug on the QIC(50) values as ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm8009102

    authors： Tietze LF,Schuster HJ,Krewer B,Schuberth I

    更新日期：2009-01-22 00:00:00

  • 3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.

    abstract：:A series of 2'- and 3'-fluorinated 2',3'-dideoxynucleosides and 3'-azido-2',3'-dideoxynucleosides were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus-1 (HIV-1) replication in MT-4 cells. Neither conversion of 3'-fluoro- or 3'-azido-2',3'-dideoxyadenosine to the correspondi...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00128a013

    authors： Van Aerschot A,Herdewijn P,Balzarini J,Pauwels R,De Clercq E

    更新日期：1989-08-01 00:00:00