Synthesis of new immunosuppressive myriocin analogs, 2-epi-myriocin, 14-deoxomyriocin, Z-14-deoxomyriocin, and nor-deoxomyriocins: their structure-activity relationships.

Abstract:

:Eight new myriocin analogs, 2-epi-myriocin, Z-14-deoxomyriocin, and nor-deoxomyriocins, and a known myriocin derivative, 14-deoxomyriocin, were synthesized from 2-deoxy-D-glucose via common intermediates in previous myriocin and Z-myriocin syntheses. The immunosuppressive activities of new myriocin analogs and Z-myriocin on mouse allogeneic mixed lymphocyte reaction were examined, and, by comparing with those of myriocin and 14-deoxomyriocin, some structure-activity relationships have been found.

authors

Yoshikawa M,Yokokawa Y,Okuno Y,Yagi N,Murakami N

doi

10.1248/cpb.42.2662

subject

Has Abstract

pub_date

1994-12-01 00:00:00

pages

2662-4

issue

12

eissn

0009-2363

issn

1347-5223

journal_volume

42

pub_type

杂志文章
  • Studies on differentiation inducers. VI. Lignan derivatives from Arctium fructus. (2).

    abstract::In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modificati...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.2300

    authors: Umehara K,Nakamura M,Miyase T,Kuroyanagi M,Ueno A

    更新日期:1996-12-01 00:00:00

  • Marine natural products. XXXIV. Trisindoline, a new antibiotic indole trimer, produced by a bacterium of Vibrio sp. separated from the marine sponge Hyrtios altum.

    abstract::A new antibiotic indole trimer named trisindoline (1) was isolated, together with a known dioxopiperazine brevianamide F (2), from the culture of a bacterium of Vibrio sp., which was separated from the Okinawan marine sponge Hyrtios altum. The structure of trisindoline (1) has been determined on the bases of physicoch...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.2449

    authors: Kobayashi M,Aoki S,Gato K,Matsunami K,Kurosu M,Kitagawa I

    更新日期:1994-12-01 00:00:00

  • Iridoid glycosides from Globularia davisiana.

    abstract::From the ethanolic extract of the aerial parts of Globularia davisiana, a new iridoid glycoside, davisioside (1), was isolated. Davisioside (1) comprises a rare iridoid aglycone structure with a saturated double bond between C-3 and C-4. Nine known iridoid glycosides, asperuloside (2), alpinoside (3), geniposide (4), ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.678

    authors: Caliş I,Kirmizibekmez H,Taşdemir D,Ireland CM

    更新日期:2002-05-01 00:00:00

  • Studies on cardiac ingredients of plants. IX. Chemical transformation of proscillaridin by utilizing its 1,4-cycloadducts as key compounds and biological activities of their derivatives.

    abstract::Three aromatic compounds (2-4) possessing a carbomethoxyl group or a dimethoxyphthaloyl group, prepared by the Diels-Alder reaction of the cardiac glycoside, proscillaridin (1), with dimethyl acetylenedicarboxylate and methyl propiolate, were transformed into alcohols, carboxylic acids and amides. The biological activ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.327

    authors: Tanase T,Murakami N,Nagai S,Ueda T,Sakakibara J,Ando H,Hotta Y,Takeya K

    更新日期:1992-02-01 00:00:00

  • Curcumin Inhibits Chondrocyte Hypertrophy of Mesenchymal Stem Cells through IHH and Notch Signaling Pathways.

    abstract::Using tissue engineering technique to repair cartilage damage caused by osteoarthritis is a promising strategy. However, the regenerated tissue usually is fibrous cartilage, which has poor mechanical characteristics compared to hyaline cartilage. Chondrocyte hypertrophy plays an important role in this process. Thus, i...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00225

    authors: Cao Z,Dou C,Dong S

    更新日期:2017-01-01 00:00:00

  • Synthesis and pharmacological evaluation of 2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinoline derivatives as specific bradycardic agents.

    abstract::Novel 1,2,3,4-tetrahydroisoquinoline derivatives bearing directly a cyclic amine at the 2-position were prepared and examined for their bradycardic activities in isolated right atria and in anesthetized rats. The structure-activity relationships (SAR) study revealed that the 2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.390

    authors: Kakefuda A,Watanabe T,Taguchi Y,Masuda N,Tanaka A,Yanagisawa I

    更新日期:2003-04-01 00:00:00

  • Synthesis and antibacterial activities of optically active substituted 1,2-dihydro-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids.

    abstract::A series of optically active substituted 1,2-dihydro-6-oxo-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids was prepared via optically active 2-methyl-4,5-difluoroindoline (10) and tested for antibacterial activities. Among them, (2S)-9-[(3R,1'S)-3-(1'-amino)ethyl-1-pyrrolidinyl]-8-fluoro-1,2-dihydro- 2- methyl-6-oxo-6H-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.1678

    authors: Tsuji K,Tsubouchi H,Ishikawa H

    更新日期:1995-10-01 00:00:00

  • Spiro-substituted piperidines as neurokinin receptor antagonists. II. Syntheses and NK2 receptor-antagonistic activities of N-[2-aryl-4-(spiro-substituted piperidin-1'-yl)butyl]carboxamides.

    abstract::In the course of our research on spiro-compounds as neurokinin receptor antagonists, N-[2-aryl-4-(spiro-substituted piperidin-1'-yl)butyl]carboxamides were designed, based on YM-35375 (3) as a lead compound, and evaluated for NK2 receptor-antagonistic activities. Some derivatives inhibited the binding of radio-labeled...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.242

    authors: Kubota H,Kakefuda A,Nagaoka H,Yamamoto O,Ikeda K,Takeuchi M,Shibanuma T,Isomura Y

    更新日期:1998-02-01 00:00:00

  • Synthesis and evaluation of 1-arylsulfonyl-3-piperazinone derivatives as factor Xa inhibitors V. A series of new derivatives containing a spiro[imidazo[1,2-a]pyrazine-2(3H),4'-piperidin]-5(1H)-one scaffold.

    abstract::We have already reported unique compounds containing a N,O-spiro acetal structure as an orally active factor Xa (FXa) inhibitor. This time, we described a N,N-spiro acetal structure as an analogue of the N,O-spiro acetal structure for an orally active FXa inhibitor. The synthesis of these analogues could be achieved i...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1535

    authors: Saitoh F,Mukaihira T,Nishida H,Satoh T,Okano A,Yumiya Y,Ohkouchi M,Johka R,Matsusue T,Shiromizu I,Hosaka Y,Matsumoto M,Ohnishi S

    更新日期:2006-11-01 00:00:00

  • Effects of several dithiocarbamates on tissue distribution and excretion of inorganic mercury in rats.

    abstract::The effects of various chelating agents, sodium N-benzyl-D-glucamine dithiocarbamate (BGD), sodium N-p-methylbenzyl-D-glucamine dithiocarbamate (MBGD), sodium N-p-hydroxymethylbenzyl-D-glucamine dithiocarbamate (HBGD), and N-p-carboxybenzyl-D-glucamine dithiocarbamate (CBGD), which were newly synthesized, and sodium N...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.757

    authors: Shimada H,Kiyozumi M,Kawagoe M,Fukudome S,Kojima S

    更新日期:1990-03-01 00:00:00

  • Cytotoxic and anti-oxidant activities of lanostane-type triterpenes isolated from Poria cocos.

    abstract::A new lanostane-type triterpene, 29-hydroxypolyporenic acid C (8), was isolated from the dried sclerotia of Poria cocos together with eight other known compounds pachymic acid (1), dehydropachymic acid (2), 3-acetyloxy-16alpha-hydroxytrametenolic acid (3), polyporenic acid C (4), 3-epi-dehydropachymic acid (5), 3-epi-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1459

    authors: Zhou L,Zhang Y,Gapter LA,Ling H,Agarwal R,Ng KY

    更新日期:2008-10-01 00:00:00

  • Syntheses of taxuspine C derivatives as functional inhibitors of P-glycoprotein, an ATP-associated cell-membrane transporter.

    abstract::UV-Irradiation of taxinine and related compounds in acetonitrile induced a smooth transannulation between the C-3 and C-11 positions without any influence from the C-2, C-9 and C-10 substituents to give tetracyclic taxuspine C derivatives in almost quantitative yields. Photochemical transannular reaction of taxoids po...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1135

    authors: Sako M,Suzuki H,Hirota K

    更新日期:1998-07-01 00:00:00

  • Contribution of prostaglandins to the renal responses to magnesium lithospermate B isolated from salviae miltiorrhizae radix.

    abstract::The involvement of prostanoids in the improvement of adenine-induced renal failure in rats by magnesium lithospermate B was studied. After intraperitoneal administration of magnesium lithospermate B to renal failure rats, the levels of glomerular filtration rate, renal plasma flow and renal blood flow were increased. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1568

    authors: Yokozawa T,Chung HY,Lee TW,Oura H,Tanaka T,Nonaka G,Nishioka I,Hirai A

    更新日期:1989-06-01 00:00:00

  • Formycin A resistant mutants due to defect in adenosine transport system in Vibrio parahaemolyticus.

    abstract::An antibiotic formycin A inhibited growth of Vibrio parahaemolyticus under certain conditions, which suggested that formycin A was taken up by cells under these conditions. We found that formycin A was transported via the adenosine transport system which we previously reported as a Na(+)-coupled cotransport system. We...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1325

    authors: Sakai-Tomita Y,Mitani Y,Tsuda M,Tsuchiya T

    更新日期:1991-05-01 00:00:00

  • Three new limonoids from Cipadessa cinerascens.

    abstract::Three new limonoids, cipadesins D--F (1--3), together with 8,15-dihydroxy-13E-labdane, beta-sitosterol and beta-daucosterol, were isolated from the leaves and bark of Cipadessa cinerascens. Their structures were elucidated by spectral evidence. X-Ray crystallographic analysis confirmed the structure of 1. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.902

    authors: Yuan XH,Li BG,Xu CX,Zhou M,Qi HY,Zhang GL

    更新日期:2007-06-01 00:00:00

  • Preparation of new nitrogen-bridged heterocycles. 49. A new access to thieno[3,4-b]indolizine derivatives.

    abstract::The title compounds, together with 3-vinylindolizine-1-carbonitriles (4-56%), were prepared in 1-18% yields from the S-alkylation of pyridinium 1-[3-ethoxycarbonyl-1-[cyanomethylthio(thiocarbonyl)]]all ylides with alkyl halides, followed by treatment of the resulting pyridinium salts with a base and then a dehydrogena...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.865

    authors: Kakehi A,Ito S,Hirata K,Zuo P

    更新日期:2000-06-01 00:00:00

  • Novel bile acids from bear bile powder and bile of geese.

    abstract::Two new bile acids, tauroselocholic acid (1) and tauroansocholic acid (2), a new natural bile acid, cygnocholic acid (3) were respectively isolated from bear bile powder Selenaretos thibetanus CUVIER and bile of geese Anser anser domesticus, together with seven known compounds. By spectrum analysis of MS, 1D and 2D NM...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.528

    authors: Bi D,Chai XY,Song YL,Lei Y,Tu PF

    更新日期:2009-05-01 00:00:00

  • Synthetic studies of vitamin D analogs. XXIV. Synthesis of active vitamin D3 analogs substituted at the 2 beta-position and their preventive effects on bone mineral loss in ovariectomized rats.

    abstract::Analogs related to 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D3 (ED-71) (4), oxa-type and carba-type analogs of vitamin D3 bearing substituents at the 2 beta-position of 1 alpha,25-dihydroxyvitamin D3 (1), were synthesized from the alpha-epoxides (6 and 13). Three analogs, ED-71 (4) and two carba-type anal...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1626

    authors: Ono Y,Watanabe H,Shiraishi A,Takeda S,Higuchi Y,Sato K,Tsugawa N,Okano T,Kobayashi T,Kubodera N

    更新日期:1997-10-01 00:00:00

  • Formulation and physicochemical characterization of imwitor 308 based self microemulsifying drug delivery systems.

    abstract::Self Microemulsifying Drug Delivery Systems (SMEDDS) are a novel alternative to the conventional transdermal delivery systems. SMEDDS are water-free systems, made up of oils and surfactants that can readily form a microemulsion upon dilution within an aqueous medium. Before SMEDDS can be used as a drug delivery system...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1332

    authors: Zargar-Shoshtari S,Wen J,Alany RG

    更新日期:2010-10-01 00:00:00

  • Formation of 8-S-L-Cysteinyladenosine from 8-Bromoadenosine and Cysteine.

    abstract::When 8-bromoadenosine was incubated with cysteine at pH 7.2 and 37°C, an exclusive product was generated. This product was identified as a cysteine substitution derivative of adenosine at the 8 position, 8-S-L-cysteinyladenosine. The reaction accelerated as pH increased from mildly acidic to basic conditions. The isol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00731

    authors: Suzuki T,Ogishi A,Shinohara T,Suito S

    更新日期:2018-01-01 00:00:00

  • Spectrophotometric and atomic absorption determination of ramipril, enalapril maleate and fosinopril through ternary complex formation with molybdenum (V)-thiocyanate (Mo(V)-SCN).

    abstract::Three different sensitive and accurate spectroscopic procedures were developed for the determination of three angiotensin-converting enzyme inhibitors, namely, ramipril, enalapril maleate and fosinopril. The first two spectrophotometric (extractive and non-extractive) procedures were based on ternary complex formation...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1521

    authors: Baraka MM,El-Sadek M,Moussa EM,Abd-Alaty NM

    更新日期:2008-11-01 00:00:00

  • Comparative molecular field analysis study of stilbene derivatives active against A549 lung carcinoma.

    abstract::A series of 43 stilbene derivatives that showed cytotoxicity against human lung carcinoma (A549) was analyzed using comparative molecular field analysis (CoMFA) for defining the hypothetic pharmacophore model. The polyoxylated stilbenes were found to be active inhibitors of tubulin polymerization. Several cis-stilbene...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.516

    authors: Kim S,Min SY,Lee SK,Cho WJ

    更新日期:2003-05-01 00:00:00

  • Preparation of Cocoa Powder-Containing Orally Disintegrating Tablets of Rebamipide (Rebamipide Chocolet) and Evaluation of Their Clinical Palatability.

    abstract::Orally disintegrating tablets (ODTs), which are administered without water, are beneficial for elderly patients and patients with dysphagia. Masking the unpleasant taste of a drug is an important factor associated with adherence of patients consuming ODTs. We prepared cocoa powder-containing ODTs of bitter-tasting reb...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00629

    authors: Takano H,Uchida S,Kashiwagura Y,Tanaka S,Hakamata A,Odagiri K,Inui N,Watanabe H,Namiki N

    更新日期:2019-01-01 00:00:00

  • Synthesis and biological activities of metabolites of mosapride, a new gastroprokinetic agent.

    abstract::In order to confirm the proposed structures of two metabolites 3 and 4 of the gastroprokinetic agent mosapride [4-amino-5-chloro-2-ethoxy-N-([4-(4-fluorobenzyl)-2-morpholinyl] methyl)benzamide, 2], the compounds were synthesized and their biological activity was examined. The structures of the metabolites were confirm...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.699

    authors: Kato S,Morie T,Yoshida N

    更新日期:1995-04-01 00:00:00

  • Kobophenol A inhibits sodium nitroprusside-induced cardiac H9c2 cell death through suppressing activation of JNK and preserving mitochondrial anti-apoptotic Bcl-2 and Mcl-1.

    abstract::Sodium nitroprusside (SNP) releases nitric oxide (NO), a powerful vasodilator, and thus widely used in intensive care unit for treating hypertension emergency. However, cardiac toxicity after SNP administration is a clinical problem. For finding a natural compound that suppressing SNP-induced cardiac toxicity, we test...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00995

    authors: Lee SR,Kwak JH,Noh SJ,Pronto JR,Ko KS,Rhee BD,Xu Z,Kim N,Han J

    更新日期:2014-01-01 00:00:00

  • Study on colon-specific 5-Fu pH-enzyme Di-dependent chitosan microspheres.

    abstract::Colon-specific drug delivery systems (CDDS) can improve the bioavailability of drug through the oral route. A novel formulation for oral administration using pH-enzyme Di-dependent chitosan mcirospheres (MS) and 5-Fu as a model drug has been investigated for colon-specific drug delivery by the emulsification/chemical ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.963

    authors: Zhao XL,Li KX,Zhao XF,Pang DH,Chen DW

    更新日期:2008-07-01 00:00:00

  • Flavonol glycosides in leaves of two Diospyros species.

    abstract::Fourteen flavonol glycosides including two new compounds were isolated from the leaves of two Diospyros plants (D. cathayensis and D. rhombifolia). The structures of isolated compounds were determined by spectroscopic analysis. The scavenging activity of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical of the isolated com...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.591

    authors: Furusawa M,Tanaka T,Ito T,Nakaya K,Iliya I,Ohyama M,Iinuma M,Murata H,Inatomi Y,Inada A,Nakanishi T,Matsushita S,Kubota Y,Sawa R,Takahashi Y

    更新日期:2005-05-01 00:00:00

  • Jatrophenone, a novel macrocyclic bioactive diterpene from Jatropha gossypifolia.

    abstract::A novel macrocyclic diterpene, jatrophenone, has been isolated from the whole plant of Jatropha gossypifolia. The structure of the compound was established by detailed studies of its one- and two-dimensional (1D and 2D) NMR spectra. The compound possesses significant antibacterial activity. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.870

    authors: Ravindranath N,Venkataiah B,Ramesh C,Jayaprakash P,Das B

    更新日期:2003-07-01 00:00:00

  • New acetylenic glucosides from Carthamus tinctorius.

    abstract::Two new acetylenic glucosides, 4',6'-acetonide-8Z-decaene-4,6-diyne-1-O-beta-D-glucopyranoside named carthamoside A(1) (1) and 4,6-decadiyne-1-O-beta-D-glucopyranoside named carthamoside A(2) (2), along with one known acetylenic glucoside, 8Z-decaene-4,6-diyne-1-O-beta-D-glucopyranoside (3), have been isolated from th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1455

    authors: Zhou YZ,Ma HY,Chen H,Qiao L,Yao Y,Cao JQ,Pei YH

    更新日期:2006-10-01 00:00:00

  • Synthesis of new N-analogous corollosporine derivatives with antibacterial activity by laccase-catalyzed amination.

    abstract::Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.781

    authors: Mikolasch A,Hessel S,Salazar MG,Neumann H,Manda K,Gōrdes D,Schmidt E,Thurow K,Hammer E,Lindequist U,Beller M,Schauer F

    更新日期:2008-06-01 00:00:00