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Volume 47, Issue 12
Displaying 1-24 of 24 articles from this issue
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Amos B. SMITH, James R. EMPFIELD1999 Volume 47 Issue 12 Pages 1671-1678
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhyllanthoside and breynin A are structurally related spiroketal glycoside natural products with potent, interesting and diverse biological activities. Due to their therapeutic potential and novel architecture, the respective aglycones, phyllanthocin and breynolide have attracted significant effort from the synthetic community. This review highlights the synthetic approaches to these targets with an emphasis on the strategy for incorporating the requisite stereogenic centers.View full abstractDownload PDF (1086K) -
Hiroyuki NAITO, Masamichi SUGIMORI, Ikuo MITSUI, Yoshihide NAKAMURA, M ...1999 Volume 47 Issue 12 Pages 1679-1684
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel pyrimidinyl pyrazole derivatives were synthesized and examined for cytotoxic and antitumor activity. Mannich reaction was employed to construct this scaffold. Among the compounds synthesized, a series of propene derivatives exhibited a potent cytotoxic activity against some tumor cell lines including multidrug resistant cell lines due to the overexpression of P-glycoprotein. The vinyl bond moiety in the scaffold was believed to be required for the cytotoxic activity. Among them, compound 14g, when administered intraperitoneally, showed potent antitumor activity against the malignant ascites caused by intraperitoneal inoculation of P388 cells in mice. This compound also showed high activity against a solid tumor Meth A mouse fibrosarcoma when administered both intraperitoneally and orally.View full abstractDownload PDF (849K) -
Shin'ichiro ONO, Yoshihisa INOUE, Tomohiro YOSHIDA, Atsuyuki ASHIMORI, ...1999 Volume 47 Issue 12 Pages 1685-1693
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis and design using molecular modeling techniques for non-peptide, low molecular weight novel fibrinogen receptor (glycoprotein IIb/IIIa : Gp IIb/IIIa) antagonists, is reported. We used a highly potent serine protease inhibitor, Nafamostat, having an amidinonaphthyl unit as the starting compound. The compounds 4-(6-amidino-2-naphthylaminocarbonyl)phenoxyacetic acid (5a) and 4-(6-amidino-2-naphthalenecarboxamido)phenoxyacetic acid (5b) inhibited adenosin-5'-diphospate (ADP)-induced aggregation of human platelet-rich plasma (PRP) with IC50 values of 0.05 and 0.07 μM, respectively, and had lost their ability to inhibit a variety of serine proteases, including thrombin, factor Xa, plasmin and trypsin.View full abstractDownload PDF (1305K) -
Shin'ichiro ONO, Tomohiro YOSHIDA, Kazuhiro MAEDA, Keigo KOSAKA, Yoshi ...1999 Volume 47 Issue 12 Pages 1694-1712
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel series of platelet receptor glycoprotein (Gp) IIb/IIIa antagonists with condensed heterocycles as their basic core was synthesized. In an in vitro assay, trans-4-(5-amidinobanzofuran-2-carboxamido)cyclohexyloxyacetic acid 17e and trans-3-[4-(5-amidinobanzofuran-2-carboxamido)cyclohexyl]propionic acid 17f produced marked inhibitions with IC50 values of 0.018 and 0.006 μM, respectively in a human platelet adenosin-5'-diphospate (ADP)-induced aggregation assay; they also exhibited a wide spectrum of inhibition toward major aggregation agonists (ADP, collagen, thrombin, PMA (tumor promoter) and arachidonic acid). These compounds were >2-3 orders of magnitude more effective in inhibiting platelet aggregation than human umbilical vein endothelial cell (HUVEC) binding. The oral administration of 10 mg/kg of either 17e and 17f to guinea pig, resulted in a 60% inhibition of ex vivo platelet aggregation after 5 h. Oral administration of ethyl trans-4-(5-amidinobenzofuran-2-carboxamido)cyclohexyloxyacetate 18e (10 mg/kg) resulted in 80% inhibition of platelet aggregation in dogs for 6 h after oral administration with a return to baseline by 24 h. Ethyl trans-3-[4-(5-amidinobenzofuran-2-carboxamido)cyclohexyl]propionate 18f (AR0598) produced 80% inhibition for 5 h after oral administration. Prodrug 18e showed a good profile in dogs with a long duration of action. 18e (AR0510) was selected as suitable clinical candidate for development as an orally active antithrombotic agent.View full abstractDownload PDF (2678K) -
Naohide HORI, Makiko FUJII, Kazuhiko IKEGAMI, Den-ichi MOMOSE, Noriyas ...1999 Volume 47 Issue 12 Pages 1713-1716
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTranilast (TL) oily gels containing UV-absorbing agents (UV absorber) were prepared, and the effect of the agents against photodegradation of TL was investigated. When 0.1% TL oily gel without UV absorber was exposed to light, TL was photochemically decomposed to the extent of 74.1% of its initial content at the end of the first hour. Although there were differences in the preventive effect on photodegradation of TL depending on the UV absorbers employed, 2-(2-benzotriazolyl)-p-cresol (BTPC) was the most effective absorber. The addition of UV absorbers to the oily gel did not affect the release of TL from the gel, the skin permeation, or the skin concentration of TL following topical application. UV absorbers added to TL oily gel penetrated into skin; however, their concentration in skin was similar to that following application of commercial sunscreen. These results suggest that the addition of UV absorbers to the oily gel of TL may be useful in preventing photodegradation of TL in the gel.View full abstractDownload PDF (705K) -
Toshiyuki MURAKAMI, Hisashi MATSUDA, Masahiro INADZUKI, Kazuhiro HIRAN ...1999 Volume 47 Issue 12 Pages 1717-1724
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absolute stereostructures of betavulgaroside II having a dioxolane-type substituent and betavulgaroside IV having an acetal-type substituent, which were isolated from the roots of Beta vulgaris L. (sugar beet, Chenopodiaceae) and exhibited hypoglycemic activity on glucose-loaded rats, were determined by the chemical correlations of betavulgarosides II and IV with a known saponin, momordin I. In these chemical correlations, the α-L-arabinopyranosyl moiety of momordin I was converted to a dioxolane-type substituent of betavulgaroside II or to an acetal-type substituent of betavulgaroside IV. Additionally, the 2'-diastereoisomer of betavulgaroside IV was synthesized from momordin I, and four acetal-type substituent analogues were also synthesized from L- and D-arabinose.View full abstractDownload PDF (1248K) -
Hisashi MATSUDA, Toshiyuki MURAKAMI, Kenichi YASHIRO, Johji YAMAHARA, ...1999 Volume 47 Issue 12 Pages 1725-1729
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe aqueous methanolic extract of an Indian natural medicine, the roots of Salacia oblonga WALL. (Celastraceae), was found to show inhibitory activity on the increase in serum glucose level in sucrose- and maltose-loaded rats. The water-soluble and ethyl acetate-soluble portions from the aqueous methanolic extract showed inhibitory activities on α-glucosidase and aldose reductase, respectively. From the water-soluble portion, potent α-glucosidase inhibitors, salacinol and kotalanol, were isolated, together with nine sugar related components, while a new friedelane-type triterpene, kotalagenin 16-acetate, was isolated from the ethyl acetate-soluble portion along with known diterpenes and triterpenes. The structure of kotalagenin 16-acetate was elucidated on the basis of physicochemical evidence. Principal components from this natural medicine were examined in terms of inhibitory activity on aldose reductase, and the diterpene and triterpene constituents, including the new kotalagenin 16-acetate, were found to be responsible components for the inhibitory activity on aldose reductase.View full abstractDownload PDF (729K) -
Yoshio TAKEUCHI, Zhaopeng LIU, Akira SATOH, Tomoki SHIRAGAMI, Norio SH ...1999 Volume 47 Issue 12 Pages 1730-1733
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel pathway for the preparation of 3, 4-dihydro-2H-1λ6-benzo[e][1, 2]thiazine 1, 1-dioxides 3 via an orthomethyl lithiation/cyclization reaction of N-acyl-o-toluenesulfonamides 5 is reported. Readily available N-acyl-o-toluenesulfonamides 5 were treated with 2 eq of n-BuLi at -78°C-0°C to give the corresponding sultams 6 in moderate to good yields. The resulting sultams 6 were converted to saturated sultams 3, which can be considered as one carbon-extended homologues of the Oppolzer sultams 1, in high yields by hydrogenation. Studies on the scope and limitation of this annulation for the preparation of sultams are discussed. Demonstration of the feasibility of using the sultams 3 templates for an electorophilic fluorinating agent is also described.View full abstractDownload PDF (648K) -
Atsuo OHIKE, Kenichi ASHIHARA, Rinta IBUKI1999 Volume 47 Issue 12 Pages 1734-1739
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the wet granulation process with a high speed mixer, the fast Fourier transform (hereinafter FFT) technique with a personal computer was adopted to perform concurrent precise analysis of the vibration to monitor the granulation process. In this study, a vibration pattern was obtained by inserting a probe into the powder layer. The specific weve pattern of the vibration was observed as granulation progressed. The frequency of the wave was equivalent to that of the impeller blades of the high speed mixer. The elemental strength of the wave at the impeller blade frequency (hereinafter ESWF) converted by FFT exhibits a good relationship with the mass median diameter of the granules. It was demonstrated that the wet granulation process can be concurrently monitored and controlled by ESWF.View full abstractDownload PDF (810K) -
Synthesis of β- and γ-Carbolines and Their N-Oxides from 2(or 3)-Ethynylindole-3(or 2)-carbaldehydesTakao SAKAMOTO, Atsushi NUMATA, Hironori SAITOH, Yoshinori KONDO1999 Volume 47 Issue 12 Pages 1740-1743
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIsoquinoline-type carbolines i.e. β-, and γ-carbolines and their N-oxides were synthesized from 2(or 3)-ethynylindole-3(or 2)-carbaldehydes, which were synthesized by electrophilic substitution with dichloromethyl methyl ether in the presence of titanium tetrachloride, or by lithiation with tert-butyllithium, followed by formylation with methyl formate.View full abstractDownload PDF (694K) -
Hisashi MATSUDA, Toshiyuki MURAKAMI, Akira IKEBATA, Johji YAMAHARA, Ma ...1999 Volume 47 Issue 12 Pages 1744-1748
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the elucidation of jujubosides A1 and C and acetyljujuboside B, novel protojujubogenin type triterpene bisdesmosides, protojujubosides A, B, and B1, were isolated from Zizyphi Spinosi Semen, the seeds of Zizyphus jujuba MILL. var. spinosa HU. The structures of protojujubosides A, B, and B1 were determined on the basis of chemical and physicochemical evidence, which included the conversion of protojujubosides to known jujubosides using enzymatic hydrolysis. Protojujubosides A and jujubosides A, B, and C were found to show potent immunological adjuvant activity.View full abstractDownload PDF (794K) -
Jian-mei HUANG, Chun-shu YANG, Hai WANG, Qiu-ming WU, Jia-ling WANG, Y ...1999 Volume 47 Issue 12 Pages 1749-1752
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new sesquiterpenes, named merrillianone (1), cyclomerrillianolide (2), merrillianolide (3), 1α-hydroxy-3-deoxypseudoanisatin (4) and 7-O-acetylanislactone B (5), were isolated from the pericarps of Illicium merrillianum, a species indigenous to southwestern China and Burma. Their structures were elucidated based on spectroscopic and chemical data. The structure of 1 was confirmed by X-ray crystallographic analysis of its acetylated derivative 1a to consist of a novel cagelike acetal and hemiacetal structure. The NMR data for compounds 2 and 3, which could not be separated due to an equilibrium mixture of keto and hemiacetal forms, were unambiguously assigned, respectively.View full abstractDownload PDF (693K) -
Hisashi MATSUDA, Hiroshi SHIMODA, Toshiaki UEMURA, Tomohiko UEDA, Johj ...1999 Volume 47 Issue 12 Pages 1753-1758
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the characterization of dihydroisocoumarin constituents, two secoiridoid glucoside complexes, called hydramacrosides A and B, were isolated from the leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The absolute stereostructures of hydramacrosides A and B were elucidated on the basis of chemical and physicochemical evidence, which included the application of the 13C-NMR glycosylation shift rule of 1, 1'-disaccharides and the modified Mosher's method. Hydramacrosides A and B exhibited an inhibitory effect on histamine release from rat mast cells induced by an antigen-antibody reaction.View full abstractDownload PDF (899K) -
Toshiyuki MURAKAMI, Junko NAKAMURA, Hisashi MATSUDA, Masayuki YOSHIKAW ...1999 Volume 47 Issue 12 Pages 1759-1764
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe saponin fraction from the seeds of the tea plant, Camellia sinensis L. var. assamica PIERRE cultivated in Sri Lanka, was found to show a potent protective effect on gastric mucosal lesions induced by ethanol in rats. Nine new acylated polyhydroxyoleanene-type triterpene oligoglycosides called assamsaponins A-I were isolated from the active saponin fraction together with three known saponins, theasaponin E1 and E2 and camellias-aponin B1. The structures of assamsaponins A-E were elucidated on the basis of chemical and physicochemical evidence. Theasaponin E1 exhibited potent gastroprotective activity.View full abstractDownload PDF (992K) -
Masato MATSUOKA, Jun SEGAWA, Isao AMIMOTO, Yasushi MASUI, Yoshifumi TO ...1999 Volume 47 Issue 12 Pages 1765-1773
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 7-substituted-6-fluoro-1-fluoromethyl-4-oxo-4H-[1, 3]thiazeto[3, 2-α]quinoline-3-carboxylic acid derivatives (2a-1) was prepared and evaluated for antibacterial activity. These compounds were obtained by deacylation of 4-benzoyloxy-2-(1-chloro-2-fluoroethyl)thio-6, 7-difluoroquinoline-3-carboxylate (10) and subsequent intramolecular cyclization followed by substitution with cyclic amines and then hydrolysis.The intramolecular cyclization reaction of 18, one of the diastereomers (17, 18) revealed that the cyclization reaction proceeded through an inversion to afford (-)-11a in good chemical and optical yield. The enantiomers of 2a were prepared from the enantiomers of 11a, which were obtained by the optical resolution of the racemate using high-performance liquid chromatography (HPLC).Compounds 2a, b showed excellent in vitro and in vivo antibacterial activity against both gram-negative and gram-positive bacteria including quinolone and Methicillin-resistant Staphylococcus aureus.View full abstractDownload PDF (1239K) -
Yoshiko NAGATA, Yoshikazu MATSUSHIMA, Noriko FUJII, Sumi FUKUDA, Hidek ...1999 Volume 47 Issue 12 Pages 1774-1777
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSQuinonoid species absorbing in the 500-nm region, which should serve as a model for the key intermediate in reactions catalyzed by pyridoxal phosphate enzymes, was formed in the reactions of pyridoxamine (PM) with pyrroloquinoline quinone (PQQ), 1, 7-phenathroline-5, 6-quinone and 4, 7-phenathroline-5, 6-quinone in alkaline methanol at 25°C. The band at around 500 nm appeared gradually and its intensity reached a maximum about 6 h after initiation of the reaction, then decreased gradually and disappeared. 1, 10-Phenathroline-5, 6-quinone which lacks pyridine nitrogen peri to the o-quinone carbonyl groups did not react with primary amines under the conditions used. Crystalline product was prepared from PM and PQQ. Absorption spectra of its methanol and water solutions were similar to the spectrum formed from the reaction of PM and PQQ with 500 nm band assigned to the quinonoid. The results of FAB mass were consistent with the formula of the ketimine and the quinonoid formed from PM and PQQ.View full abstractDownload PDF (587K) -
Masayuki EBISAWA, Hiroki UMEMIYA, Kiminori OHTA, Hiroshi FUKASAWA, Emi ...1999 Volume 47 Issue 12 Pages 1778-1786
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral dibenzodiazepine derivatives were identified as novel retinoid X receptor (RXR) antagonists on the basis of inhibitory activity on retinoid-induced cell differentiation of human promyelocytic leukemia cells HL-60 and transactivation assay using retinoic acid receptors (RARs) and RXRs in COS-1 cells. 4-(5H-2, 3-(2, 5-Di-methyl-2, 5-hexano)-5-n-propyldibenzo[b, e][1, 4]diazepin-11-yl)benzoic acid (HX603, 6c) is an N-n-propyl derivative of an RXR pan-agonist HX600 (6a), and exhibited RXR-selective antagonistic activity. Similar RXR-antagonistic activities were observed with 4-(5H-2, 3-(2, 5-dimethyl-2, 5-hexano)-5-methyl-8-nitrodibenzo[b, e][1, 4]diazepin-11-yl)benzoic acid (HX531, 7a) and 4-(5H-10, 11-dihydro-5, 10-dimethyl-2, 3-(2, 5-dimethyl-2, 5-hexano)-dibenzo[b, e][1, 4]diazepin-11-yl)benzoic acid (HX711, 8b), which also inhibited transactivation of RARs induced by an RAR agonist, Am80. These compounds inhibited HL-60 cell differentiation induced by the combination of a low concentration of the retinoid agonist Am80 with an RXR agonist (a retinoid synergist, HX600). These results indicated that HX603 (6c), and the related RXR antagonists inhibit the activation of RAR-RXR heterodimers as well as RXR homodimers, which is a distinct characteristic different from that of the known RXR antagonist, LG100754 (9).View full abstractDownload PDF (1385K) -
Takashi MICHIDA, Eriko OSAWA, Yumiko YAMAOKA1999 Volume 47 Issue 12 Pages 1787-1789
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of the formation of 2, 7-disubstituted phenazine in the oxidation of 4'-substituted benzen-sulfenanilide was studied by employing the PM3 method. Calculation of the total energy suggested that the homolytic cleavage of the S-N bond of cation radical (A) derived from benzenesulfenanilides was not a spontaneous reaction at room temperature. The following mechanism has been suggested. Dimerization of A followed by proton migration gives (4-substituted phenyl) (5-substituted-2-(phenylthioamino)phenylthioamine (5), which is oxidized to give a cation, which is then cyclized to give 2, 7-disubstituted 5, 10-phenylthio-5, 10-dihydrophenazine (6). The acid hydrolysis of 6 gives diphenylthiosulfinate and 2, 7-disubstituted-5, 10-dihydrophenazine, and the latter is oxidized to 2, 7-disubstituted phenazine by dissolved oxygen in the reaction solution.View full abstractDownload PDF (454K) -
Kagayaki NATSUKA, Yoshinori NISHIKAWA, Hideo NAKAMURA1999 Volume 47 Issue 12 Pages 1790-1793
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo ascertain roles of the two basic nitrogen atoms in 1-substituted 4-[2-(3-hydroxyphenyl)-1-phenylethyl]-piperazine derivatives (1) in the expression of opioid agonist and antagonist activities, a methine group (CH) was isosterically substituted for nitrogen atom at the 1-position (N-1) in compound 1 to obtain 4-substituted 1-[2-(3-hydroxyphenyl)-1-phenylethyl]piperidine derivatives (2). Their analgesic action and ability to produce physical dependence (jump-producing activity) as the μ-opioid receptor specific in vivo actions, and narcotic antagonist action in mice were compared with those of compound 1. Results of this study showed that, in cases of the racemate and the (S)-(+) enantiomer, opioid agonist activities (analgesic and jump-producing activities) were not greatly affected by the methine-substitution for N-1 in compound 1, but that the narcotic antagonist activity of the (R)-(-) enatiomer was abolished by this substitution. It thus appears that N-1 in compound 1 contributes to the expression of narcotic antagonist activity, whereas the nitrogen atom at the 4-position corresponds to the tyramine moiety necessary for the expression of μ-opioid agonist activity.View full abstractDownload PDF (626K) -
Jun ANDO, Akiko MIYAZONO, Xing-Hua ZHU, Tsuyoshi IKEDA, Toshihiro NOHA ...1999 Volume 47 Issue 12 Pages 1794-1796
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOur search for bioactive steroidal glycosides among solanaceous plants has led to the isolation and characterization of four new glycosides, β-chacotriosyl (25R, 26R)-spirost-5-ene-3β, 17α, 26-triol (1), the 26-O-methyl derivative (2) of 1, 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)] β-D-glucopyranoyl (25R, 26R)-26-O-methyl-spirost-5-ene-3β, 17α, 26- triol (3) and β-chacotriosyl (22ψ, 25R)-furost-5-ene-3β, 17α, 22, 26-tetraol 26-O-β-D-glucopyranoside (4) from the fruits of Solanum nodiflorum.View full abstractDownload PDF (538K) -
Tianpei FAN, Zhida MIN, Munekazu IINUMA1999 Volume 47 Issue 12 Pages 1797-1798
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel royleanones, bungone A (1) and B (2) have been isolated from the stem of Clerodendrum bungei. The structures of these two compounds [9, 10-dihydro-3, 4, 9-trimethyl phenanthro[3, 2-b]pyran (7H)-7, 12(8H)-dione (bungone A) and 9, 10-dihydro-8-hydroxymethyl-3, 4, 9-trimethyl phenanthro[3, 2-b]pyran (2H)-7, 12-dione (bungone B)] were determined mainly on the spectral analysis.View full abstractDownload PDF (360K) -
Shosuke SOFUKU, Akiko HOSHIDA, Takehiro SHIMADA, Yoichi TAKADA, Takash ...1999 Volume 47 Issue 12 Pages 1799-1801
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of cyclic RGD peptides with 8-10 residues cyclized by an amide bond and the relationship between their structure and activity (i.e. circular dichroism spectrum and inhibition of platelet aggregation) are reported. The linear peptides were synthsized by the solution method and their cyclization was performed in high dilution using DPPA.View full abstractDownload PDF (492K) -
Che Shun YAO, Toshiyuki KIMURA, Kazuhito WATANABE, Shigemi KONDO, Ing ...1999 Volume 47 Issue 12 Pages 1802-1804
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN3-Substituted derivatives of 2', 3'-O-isopropylideneuridine (1) were synthesized and their pharmacological effects on the central nervous system (CNS) examined using mice. Methyl (2), ethyl (3), propyl (4), butyl (5), allyl (6), benzyl (7), o-, m-, p-xylyls (8, 9, 10), and α-phenylethyl (11) derivatives of 1 were administered to mice by intracerebroventricular (i.c.v.) injection for evaluating hypnotic activity, pentobarbital-induced sleep prolongation, and spontaneous activity as indices. Only 3 possessed hypnotic activity by i.c.v. injection at the dose of 2.0 μmol/mouse. Compounds 3, 4, and 10 significantly showed synergism with a barbiturate, indicating that the derivatives have some CNS depressant effects. Moreover, 3 and 4 caused decrease in the spontaneous activity of mice, even at low doses. The present study indicated that substitution by ethyl, propyl, and p-xylyl groups at the N3-position of 2', 3'-O-isopropylideneuridine imparted the CNS depressant effects.View full abstractDownload PDF (575K) -
Nagako KUWABARA, Hiroyuki HAYASHI, Noriko HIRAMATSU, Tominari CHOSHI, ...1999 Volume 47 Issue 12 Pages 1805-1807
Published: December 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew total syntheses of renierol (3), renierol acetate (4), and renierol propionate (5) were completed by the synthesis of 5-oxygenated isoquinoline (6) based on the thermal electrocyclic reaction of the 1-azahexatriene system followed by regioselective oxidations of 5-hydroxyisoquinolines (6).View full abstractDownload PDF (486K)
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