当前位置： SCI文献检索 > CHEMICAL & PHARMACEUTICAL BULLETIN期刊下所有文献 > Purines. L. Synthesis and antileukemic activity of the antibiotic guanine 7-oxide and its 9-substituted derivatives.

Purines. L. Synthesis and antileukemic activity of the antibiotic guanine 7-oxide and its 9-substituted derivatives.

Abstract：

:A full account is given of the first chemical synthesis of the antitumor antibiotic guanine 7-oxide (5) and its 9-substituted derivatives (24a--k and 26). Coupling of appropriate primary amines (17a--e, g--k) with phenacyl bromide (16) produced, after treatment with HCl, the corresponding N-substituted phenacylamine hydrochlorides (18a--e, g--k). A similar phenacylation of 4-amino-l-butanol (21) failed to give the desired compound 18f, so that 21 was heated with 2-bromomethyl-2-phenyl-1,3-dioxolane (20) at 150-155 degrees C for 3h to furnish, after treatment with HCl, the amino ketal hydrochloride 22 in 40% yield. Deketalization of 22 with hot 2 N aqueous HCl afforded 18f in 96% yield. Condensations of the free bases, generated in situ from the hydrochlorides 18a--l and 1N aqueous NaOH, with the chloropyrimidinone 6 were effected in aqueous EtOH at the boiling point for 20 min or at 25-30 degrees C for 3-24h, giving the 6-phenacylamino-4-pyrimidinones 19a-l in 54-90% yields. On treatment with 2N aqueous NaOH at room temperature for 10-60 min, the nitropyrimidinones 19a--k cyclized to provide the 9-substituted guanine 7-oxides 24a--k in 61-98% yields. A similar alkali-treatment of 191 failed to yield guanine 7-oxide (5). However, removal of the 9-(arylmethyl) group from 24i--k was effected with conc. H2SO4 at room temperature for 1-3h in the presence of toluene, producing the target N-oxide 5 in 56-89% yields.(ABSTRACT TRUNCATED AT 250 WORDS)

journal_name

Chem Pharm Bull (Tokyo)

journal_title

Chemical & pharmaceutical bulletin

authors

Ogawa K,Nishii M,Inagaki J,Nohara F,Saito T,Itaya T,Fujii T

doi

10.1248/cpb.40.343

subject

Has Abstract

pub_date

1992-02-01 00:00:00

pages

343-50

issue

2

eissn

0009-2363

issn

1347-5223

journal_volume

40

pub_type

杂志文章

相关文献

CHEMICAL & PHARMACEUTICAL BULLETIN文献大全
  • Constituents of the Vietnamese medicinal plant Orthosiphon stamineus.

    abstract：:From the MeOH extract of the aerial part of Vietnamese Orthosiphon stamineus, five new isopimarane-type diterpenes [orthosiphols F-J (1-5)] and two new diterpenes [staminols A (6) and B (7)] with a novel carbon-framework, to which we proposed the name "staminane", and three new highly-oxygenated staminane-type diterpe...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.48.1711

    authors： Tezuka Y,Stampoulis P,Banskota AH,Awale S,Tran KQ,Saiki I,Kadota S

    更新日期：2000-11-01 00:00:00

  • Studies on the constituents of Cimicifuga species. XXVIII. Cycloart-7-enol glycosides from the underground parts of Cimicifuga simplex Wormsk.

    abstract：:Four new cycloart-7-ene triterpenol arabinosides, bugbanosides C-F, were isolated from the underground parts of Cimicifuga simplex Wormsk. (Ranunculaceae). The structures were elucidated as 12beta-acetoxy-3beta,15alpha,-24R,25-tetrahydroxy-16,23-dione-cycloart-7-ene 3-O-alpha-arabinopyranoside, 12beta-acetoxy-24R,25-e...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.49.437

    authors： Kusano A,Shibano M,Tsukamoto D,Kusano G

    更新日期：2001-04-01 00:00:00

  • Detection and identification of loline and its analogues in horse urine.

    abstract：:Several kinds of loline-type alkaloids, norloline, loline, N-acetylnorloline, N-acetylloline, N-formylnorloline, N-formylloline and N-methylloline were detected in the urine of race-horses. Furthermore, a new compound of the alkaloids, N-senecioylnorloline, was also found and identified. These compounds were mainly id...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.39.964

    authors： Takeda A,Suzuki E,Kamei K,Nakata H

    更新日期：1991-04-01 00:00:00

  • Studies on cognitive enhancing agents. I. Antiamnestic and antihypoxic activities of 2-dimethylaminoethyl ethers and related compounds.

    abstract：:N-(2-Dimethylaminoethyl)carboxamide (1a-d), 2-dimethylaminoethyl alkyl ether (2a, b), and 2-dimethylaminoethyl 2-hydroxy-2-phenethyl ether (3a-c) and its amino and methylene analogues (3d, 4) have been screened for antiamnestic and antihypoxic activities in mice. A clear reversing effect on electroconvulsive shock-ind...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.43.1483

    authors： Ono S,Yamafuji T,Chaki H,Todo Y,Maekawa M,Kitamura K,Tai M,Narita H

    更新日期：1995-09-01 00:00:00

  • Antisweet natural products. VIII. Structures of hodulosides VI--X from Hovenia dulcis Thunb. var. tomentella Makino.

    abstract：:From the Fresh leaves of Hovenia dulcis Thunb. var. tomentella Makino, five five new dammarane glycosides named hodulosides VI-X (1-5) were isolated. Their structures were determined on the basis of chemical and spectral evidence. Hodulosides VII-X showed antisweet activities. ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.41.1722

    authors： Yoshikawa K,Nagai Y,Yoshida M,Arihara S

    更新日期：1993-10-01 00:00:00

  • Compositional analysis of copoly (DL-lactic/glycolic acid) (PLGA) by pyrolysis-gas chromatography/mass spectrometry combined with one-step thermally assisted hydrolysis and methylation in the presence of tetramethylammonium hydroxide.

    abstract：:Rapid and precise compositional analysis of copoly (DL-lactic/glycolic acid) (PLGA) was performed by pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) combined with one-step hydrolysis and methylation in the presence of tetramethylammonium hydroxide (TMAH). Pyrolysis of PLGA with TMAH gave two characteristic p...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.49.203

    authors： Urakami K,Higashi A,Umemoto K,Godo M,Watanabe C,Hashimoto K

    更新日期：2001-02-01 00:00:00

  • New iridoids from Gelsemium species.

    abstract：:Four new iridoids structurally related to gelsemide (5) were isolated from two Loganiaceous plants, Gelsemium elegans and G. rankinii. Among them, GEIR-1 (1) has a novel tetracyclic caged structure. ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.56.870

    authors： Kogure N,Ishii N,Kobayashi H,Kitajima M,Wongseripipatana S,Takayama H

    更新日期：2008-06-01 00:00:00

  • Paracetamol-propyphenazone interaction and formulation difficulties associated with eutectic formation in combination solid dosage forms.

    abstract：:Polymorphic behaviours of paracetamol and propyphenazone and interaction between these two compounds were investigated using differential scanning calorimetry (DSC), X-ray powder diffraction and Fourier transform-infrared (FT-IR)-spectroscopy. Binary mixtures containing various ratios of the compounds were prepared as...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.47.302

    authors： Zalac S,Khan MZ,Gabelica V,Tudja M,Mestrović E,Romih M

    更新日期：1999-03-01 00:00:00

  • Synthesis and HIV-1 integrase inhibition of novel bis- or tetra-coumarin analogues.

    abstract：:Present studies were undertaken on the preparation of synthetic analogues of bis- or tetra-coumarins and their activity against HIV-1 integrase (HIV-1 IN). Among these coumarin analogues, compounds 14, 16 and 18 were found to be potent molecules against HIV-1 IN at IC50 values of 0.96, 0.58, and 0.49 microM, respectiv...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.55.1740

    authors： Chiang CC,Mouscadet JF,Tsai HJ,Liu CT,Hsu LY

    更新日期：2007-12-01 00:00:00

  • A novel method for estimation of transition temperature for polymorphic pairs in pharmaceuticals using heat of solution and solubility data.

    abstract：:A novel method for thermodynamic stability studies of polymorphic drug substances has been developed. In order to estimate the transition temperature for an enantiotropic polymorphic pair, a formula for calculating the temperature at which the solubilities of each polymorph become equal has been derived with heat of s...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.50.263

    authors： Urakami K,Shono Y,Higashi A,Umemoto K,Godo M

    更新日期：2002-02-01 00:00:00

  • Percutaneous absorption of clonazepam in rabbit.

    abstract：:The percutaneous (p.c.) absorption of clonazepam (CZP), an antiepileptic drug, was investigated in rabbits. CZP was efficiently absorbed from a gel ointment (0.5% CZP, 1g, 9 cm2) with Azone and therapeutic plasma concentrations were maintained for 27 h. The bioavailability of CZP from the gel ointment was 47.2 +/- 3.1...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.37.442

    authors： Ogiso T,Ito Y,Iwaki M,Yamamoto Y

    更新日期：1989-02-01 00:00:00

  • Physical characteristics of freeze-dried griseofulvin-lipids nanoparticles.

    abstract：:We have attempted to prepare micronized drug particles and to maintain the micronized state long-term in order to improve the solubility of a practically insoluble drug, griseofulvin (GF). GF nanoparticles (GFNPs) prepared by high-pressure homogenization were micronized to about 45 nm (mean particle size). GFNPs were ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.54.181

    authors： Kamiya S,Nozawa Y,Miyagishima A,Kurita T,Sadzuka Y,Sonobe T

    更新日期：2006-02-01 00:00:00

  • Separation of sympathomimetic amines of abuse and related compounds by micellar electrokinetic chromatography.

    abstract：:Separation of twelve sympathomimetic amines and related compounds by micellar electrokinetic chromatography (MEKC) with UV absorbance detection is described. These amines were well separated within 25 min using 50 mM sodium tetraborate solution containing 15 mM sodium dodecylsulfate (SDS) of pH 9.3 as a running soluti...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.49.905

    authors： Kuroda N,Sato D,Ohyama K,Wada M,Nakahara Y,Nakashima K

    更新日期：2001-07-01 00:00:00

  • Preparation of 4-pentenoic acid ester of Neu5Ac and 4-pentenyl glycoside of Neu5Ac and their application to glycosylation.

    abstract：:Novel sialosyl donors, 4-pentenoic acid ester of N-acetylneuraminic acids (Neu5Ac) and 4-pentenyl glycoside of Neu5Ac were successfully prepared from the corresponding per-O-acetylated 2-hydroxy and 2-chloro derivatives of Neu5Ac, respectively and applied to the synthesis of O-sialosides. ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.53.1490

    authors： Ikeda K,Fukuyo J,Sato K,Sato M

    更新日期：2005-11-01 00:00:00

  • Crystal structure of the alcoholates and the ansolvate of PNU-97018, an angiotensin II receptor antagonist.

    abstract：:The title compound, PNU-97018 [systemic name: 2-butyl-3,6,7,8,9,11-hexahydro-6,9-dimethyl-3-([2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl)-6,9-ethano-4H-imidazo[4,5-d]-pyridazino[1,2-a]pyridazin-4-one] is a newly developed angiotensin II receptor antagonist. The compound and its methanolate and ethanolate were ch...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.50.1022

    authors： Ishii H,Yamaguchi K,Seki H,Sakamoto S,Tozuka Y,Oguchi T,Yamamoto K

    更新日期：2002-08-01 00:00:00

  • Syntheses and Biological Evaluation of Novel Hydroxamic Acid Derivatives Containing Purine Moiety as Histone Deacetylase Inhibitors.

    abstract：:The novel hydroxamates containing purine scaffold were designed, synthesized and screened for their biological activities as histone deacetylase (HDAC) inhibitors. Some of them exhibited excellent acti-HDACs activities and antiproliferative activities, the most promising compound was 7m'. Western blot analysis indicat...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.c17-00997

    authors： Xu Z,Yang Y,Mai X,Liu B,Xiong Y,Feng L,Liao Y,Zhang Y,Wang H,Ouyang L,Liu S

    更新日期：2018-01-01 00:00:00

  • Regioselective synthesis of pyrazolo[4,5-g]pyrido[1,2-a]benzimidazoles: cytotoxic derivatives of pyrido[1,2-a]benzimidazolic ring system.

    abstract：:N-1 and N-2 substituted pyrazolo[4,5-g]pyrido[1,2-a]benzimidazoles were prepared regioselectively, and cytotoxicities evaluated in vitro against K562 and HL60 cells. All compounds displayed weaker activity than doxorubicin against sensitive lines, but showed the same activity against resistant cell lines (multidrug re...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.46.1820

    authors： Dupuy M,Pinguet F,Blache Y,Chavignon O,Teulade JC,Chapat JP

    更新日期：1998-11-01 00:00:00

  • Effect of aclacinomycin on lipid peroxide levels in tissues of mice.

    abstract：:We have examined the lipid peroxide levels in aclacinomycin (ACM)-treated mice by using adriamycin (ADR) as a comparative drug. There was no increase in the lipid peroxide level of the heart at either 3h or 4d after ACM administration (15 mg/kg, i.p.), although the level in the heart of ADR-treated mice was elevated t...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.37.3412

    authors： Sazuka Y,Yoshikawa K,Tanizawa H,Takino Y

    更新日期：1989-12-01 00:00:00

  • Schisandrosides A-D, Dibenzocyclooctadiene Lignan Glucosides from the Roots of Schisandra chinensis.

    abstract：:Four new dibenzocyclooctadiene lignan glucosides, schisandrosides A-D (1-4), as well as two known rare nortriterpenoids, micrandilactone C (5) and propindilactone Q (6), were isolated from the roots of Schisandra chinensis BAILLON (Schisandraceae). The structure of compounds 1-4 were elucidated by physical and spectro...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.c15-00400

    authors： Kim HM,Ryu B,Lee JS,Choi JH,Jang DS

    更新日期：2015-01-01 00:00:00

  • Proton nuclear magnetic resonance studies of the complexation of zinc(II) with glycyl-L-histidylglycine.

    abstract：:The complexation of Zn(II) with glycyl-L-histidylglycine and its deuterated derivatives, glycyl-d2-L-histidylglycine and glycyl-L-histidylglycine-d2, was studied by proton nuclear magnetic resonance spectroscopy over the pD range, from 3.4 to 11.0, at 25 degrees C. Addition of Zn(II) to the peptide made the resonances...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.43.2042

    authors： Ueda J,Hanaki A,Yoshida N,Nakajima T

    更新日期：1995-12-01 00:00:00

  • The reaction of (4R,5R)- and (4S,5S)-4,5-epoxy-2(E)-hexenoates and secondary amines.

    abstract：:A reaction of methyl (4R,5R)-4,5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R,5R)-4,5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S,5R)-4-N-benzyl-methylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.49.849

    authors： Saotome C,Ono M,Akita H

    更新日期：2001-07-01 00:00:00

  • Deoxymanoalides from the nudibranch Chromodoris willani.

    abstract：:Two sesterterpenes, deoxymanoalide (1) and deoxysecomanoalide (2), were isolated from the nudibranch Chromodoris willani collected in Okinawa and their structures determined on the basis of spectroscopic data and chemical conversions. The mollusk feeds on a sponge containing manoalide (3) and secomanoalide (4) and is ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.57.885

    authors： Uddin MH,Otsuka M,Muroi T,Ono A,Hanif N,Matsuda S,Higa T,Tanaka J

    更新日期：2009-08-01 00:00:00

  • Study of the melt pelletization process focusing on the micromeritic property of pellets.

    abstract：:Melt pelletization of lactose 450 M was carried out in an 8-l high shear mixer using PEG 3000 as the meltable binder. The pore size and size distribution of the melt pellets were determined using mercury intrusion porosimetry. The pore size distribution of melt pellets was found to be bimodal. With a higher binder con...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.48.1639

    authors： Wong TW,Chan LW,Heng PW

    更新日期：2000-11-01 00:00:00

  • The quantitative prediction of bitterness-suppressing effect of sweeteners on the bitterness of famotidine by sweetness-responsive sensor.

    abstract：:The purpose of the present study was the quantitative prediction of the bitterness-suppressing effect of sweeteners (sucrose or sugar alcohols) on the bitterness of famotidine (or quinine sulfate as control) solutions using an artificial taste sensor. Firstly, we examined the response characteristics of the sensor res...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 临床试验,杂志文章

    doi：10.1248/cpb.55.739

    authors： Hashimoto Y,Matsunaga C,Tokuyama E,Tsuji E,Uchida T,Okada H

    更新日期：2007-05-01 00:00:00

  • Synthesis and Diels-Alder reactivity of ortho-carbazolequinones.

    abstract：:Oxidation of 2- and 3-hydroxycarbazoles with Frémy's salt gave the corresponding ortho-carbazolequinones. These molecules react as carbodienophiles in Diels-Alder reaction with 1-acetoxy-1,3-butadiene and 1,3-cyclopentadiene to provide the novel benzocarbazolequinone structures 15, 16, 18 and 19. ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.52.1114

    authors： Compain-Batissou M,Latreche D,Gentili J,Walchshofer N,Bouaziz Z

    更新日期：2004-09-01 00:00:00

  • Decomposition of linear dodecylbenzenesulfonate by simultaneous treatment with ozone and ultraviolet irradiation: rapid disappearance of formed mutagens.

    abstract：:The decomposition products and mutagenic activity in Salmonella typhimurium strains TA98, TA100 and TA104 in the presence and absence of S9 mix of linear dodecylbenzenesulfonate (DBS) in aqueous solution after ozone treatment alone or simultaneous treatment with ozone and ultraviolet (UV) irradiation (ozone/UV treatme...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.40.1597

    authors： Murakami K,Matsumoto H,Kinouchi T,Ohnishi Y

    更新日期：1992-06-01 00:00:00

  • Syntheses and antiulcer activities of 2-aminonorbornene derivatives.

    abstract：:2,2,-Disubstituted norbornenes (1, 2), 2,2-Disubstituted norbornane (3), 2,2,3-trisubstituted norbornenes (4, 5), oxanorbornenes (6) and azanorbornenes (7) were synthesized by the Diels-Alder reaction using alpha, beta-dehydroamino acids as a key step, and their antiulcer activities were examined. The oxazolidine deri...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.40.102

    authors： Yamazaki H,Horikawa H,Nishitani T,Iwasaki T,Nosaka K,Tamaki H

    更新日期：1992-01-01 00:00:00

  • A novel analytical method for pharmaceutical polymorphs by terahertz spectroscopy and the optimization of crystal form at the discovery stage.

    abstract：:A novel analytical method for the determination of pharmaceutical polymorphs was developed using terahertz spectroscopy. It was found out that each polymorph of a substance showed a specific terahertz absorption spectrum. In particular, analysis of the second derivative spectrum was enormously beneficial in the discri...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.58.76

    authors： Ikeda Y,Ishihara Y,Moriwaki T,Kato E,Terada K

    更新日期：2010-01-01 00:00:00

  • Synthesis and antiviral activity of phthiobuzone analogues.

    abstract：:A series of phthiobuzone analogs, prepared from potassium phthalimide or phthalandione, have been evaluated for their antiviral activities. Among the candidates, compounds 5j and 5k, which contain the substituted 4-halogenated phenyl ring at N-4',4'' position, show more potent antiviral activity than phthiobuzone agai...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.58.208

    authors： Yang YJ,Zhao JH,Pan XD,Zhang PC

    更新日期：2010-02-01 00:00:00

  • Dealkylation of N-nitrosodibenzylamine by metalloporphyrin/oxidant model systems for cytochrome P450.

    abstract：:N-Nitrosodialkylamines are alkylating carcinogens which are metabolically activated to alpha-hydroxy nitrosamines through oxidative dealkylation by cytochrome P450. In this study, the dealkylation step in the activation of N-nitrosodibenzylamine (NDBz) was investigated with metalloporphyrin/oxidant model systems under...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.43.2173

    authors： Okochi E,Mochizuki M

    更新日期：1995-12-01 00:00:00