当前位置： SCI文献检索 > CHEMICAL & PHARMACEUTICAL BULLETIN期刊下所有文献 > Molecular geometry and physiochemical characteristics of selected anilinoquinolines, indolo[3,2-c]quinolines and tetrahydroindolo[3,2-d]benzazepines.

Molecular geometry and physiochemical characteristics of selected anilinoquinolines, indolo[3,2-c]quinolines and tetrahydroindolo[3,2-d]benzazepines.

Abstract：

:The molecular geometry, acid dissociation constants and partition coefficients of the anilinoquinoline (I), indolo[3,2-c]quinoline (II) and tetrahydroindolo[3,2-d] [1]benzazepine (III) ring systems have been determined using representative compounds: 7-chloro-4-(p-anisidino)quinoline (Ia), 3-chloro-8-methoxy-11H-indolo[3,2-c]-quinoline (IIa) and 3-chloro-9-methoxy-5,6,7,12-tetrahydroindolo[3,2-d] [1]benzazepine (IIIa). Ring systems II and III are cyclic analogues of I. The minimum energy conformation was determined by molecular mechanics. Compound IIa is the most planar and conformationally restricted, followed by IIIa and Ia. The acid dissociation constants (pKa) were determined by the solubility method. The ring nitrogen of Ia is most basic, followed by that of IIa and IIIa. The partition coefficient (log P) was determined between octanol and appropriate aqueous buffers by the shaken flask method. Hydrophobicity decreases in the order of Ia > IIa > IIIa. Factors contributing to the different molecular geometry, pKa and hydrophobicity of these related compounds are discussed. The present study may contribute to the design of better drugs with ring system I, II or III.

journal_name

Chem Pharm Bull (Tokyo)

journal_title

Chemical & pharmaceutical bulletin

authors

Koh HL,Go ML,Ngiam TL

doi

10.1248/cpb.42.1084

subject

Has Abstract

pub_date

1994-05-01 00:00:00

pages

1084-7

issue

5

eissn

0009-2363

issn

1347-5223

journal_volume

42

pub_type

杂志文章

相关文献

CHEMICAL & PHARMACEUTICAL BULLETIN文献大全
  • Novel water-soluble sedative-hypnotic agents: isoindolin-1-one derivatives.

    abstract：:We developed new intravenous sedative-hypnotic compounds with the isoindolin-1-one skeleton focusing on the water-soluble property and in vivo safety. We synthesized approximately 170 derivatives and evaluated their hypnotic effects by intravenous administration of the compounds to mice. A series of the 2-phenyl-3-[2-...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.55.1682

    authors： Kanamitsu N,Osaki T,Itsuji Y,Yoshimura M,Tsujimoto H,Soga M

    更新日期：2007-12-01 00:00:00

  • Ginseng Saponins in Different Parts of Panax vietnamensis.

    abstract：:Chemical and pharmacological studies of Panax vietnamensis (Vietnamese ginseng; VG) have been reported since its discovery in 1973. However, the content of each saponin in different parts of VG has not been reported. In this study, 17 ginsenosides in the different underground parts of P. vietnamensis were analyzed by ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.c15-00369

    authors： Le TH,Lee GJ,Vu HK,Kwon SW,Nguyen NK,Park JH,Nguyen MD

    更新日期：2015-01-01 00:00:00

  • Three new ingol diterpenes from Euphorbia nivulia: evaluation of cytotoxic activity.

    abstract：:The latex of Euphorbia nivulia afforded three new ingol diterpenes, 3-acetyl-8-methoxyl-7-angolyl-12-hydroxylingol (7), 3,12-diacetyl-7-hydroxy-8-methoxylingol (8), and 3,12-diacetyl-7-angolyl-8-hydroxylingol (9) along with five known ingol diterpenes 2-6 and a known triterpene cyclonivulinol (1). Their structures wer...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.51.431

    authors： Ravikanth V,Lakshmi Niranjan Reddy V,Vijender Reddy A,Ravinder K,Prabhakar Rao T,Siva Ram T,Anand Kumar K,Prakesh Vamanarao D,Venkateswarlu Y

    更新日期：2003-04-01 00:00:00

  • The combination effect of L-arginine and NaCl on bitterness suppression of amino acid solutions.

    abstract：:The purpose of the present study was to quantify the degree of suppression of the bitterness of two amino acids (L-isoleucine (L-Ile), and L-phenylalanine (L-Phe)) which could be achieved by the addition of various test chemicals, and to examine the mechanism of this bitterness suppression. The test chemicals used wer...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.52.172

    authors： Ogawa T,Nakamura T,Tsuji E,Miyanaga Y,Nakagawa H,Hirabayashi H,Uchida T

    更新日期：2004-02-01 00:00:00

  • Synthetic studies of the lichen macrolide lepranthin. Stereoselective synthesis of the diolide framework based on regioselective epoxide-opening reactions.

    abstract：:Stereoselective synthesis of the 16-membered diolide 27, a fully functionalized congener of lepranthin (1), is described. The requisite five asymmetric carbon centers in monomer 23 were constructed in a highly stereoselective manner by using different epoxide-opening reactions of α,β-unsaturated γ,δ-epoxy esters and e...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.59.525

    authors： Takada H,Nagumo S,Yasui E,Mizukami M,Miyashita M

    更新日期：2011-01-01 00:00:00

  • Biotransformation of chrysin and apigenin by Cunninghamella elegans.

    abstract：:Biotransformation of chrysin by Cunninghamella elegans NRRL 1392 produced apigenin, apigenin 7-sulfate, apigenin 7,4'-disulfate, and a new metabolite identified as chrysin 7-sulfate. On the other hand, fermentation of apigenin, using the same microorganism, yielded apigenin 7-sulfate and apigenin 7,4'-disulfate. The s...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.53.671

    authors： Ibrahim AR

    更新日期：2005-06-01 00:00:00

  • Diarylureas and diarylamides with pyrrolo[2,3-d]pyrimidine scaffold as broad-spectrum anticancer agents.

    abstract：:A series of diarylureas and diarylamides possessing pyrrolo[2,3-d]pyrimidine scaffold was designed and synthesized. The in vitro antiproliferative activities of a selected group of the target compounds against NCI-60 cell line panel were tested and compared with Sorafenib and Imatinib as reference compounds. Most of t...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.c13-00249

    authors： El-Gamal MI,Oh CH

    更新日期：2014-01-01 00:00:00

  • NO-NSAIDs. Part 3: nitric oxide-releasing prodrugs of non-steroidal anti-inflammatory drugs.

    abstract：:In continuation of our efforts to discover novel nitric oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) as potentially "Safe NSAIDs," we report herein the design, synthesis and evaluation of 21 new NO-NSAIDs of commonly used NSAIDs such as aspirin, diclofenac, naproxen, flurbiprofen, ketoprofen, suli...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.60.465

    authors： Borhade N,Pathan AR,Halder S,Karwa M,Dhiman M,Pamidiboina V,Gund M,Deshattiwar JJ,Mali SV,Deshmukh NJ,Senthilkumar SP,Gaikwad P,Tipparam SG,Mudgal J,Dutta MC,Burhan AU,Thakre G,Sharma A,Deshpande S,Desai DC,Dubash

    更新日期：2012-01-01 00:00:00

  • Self-association of telomeric short oligodeoxyribonucleotides containing a dG cluster.

    abstract：:Oligonucleotides containing a dG cluster, d(TmGnTm), are models of single-stranded parts of telomeric deoxyribonucleic acid and substitutes for poly(dG). Electrophoretic and spectroscopic analyses of the oligomers indicate that the oligomers can form two alternative structures, single- and quadruple-stranded helices, ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.39.2207

    authors： Shida T,Yokoyama K,Tamai S,Sekiguchi J

    更新日期：1991-09-01 00:00:00

  • Bio-active Natural Products with TRAIL-Resistance Overcoming Activity.

    abstract：:Tumor necrosis factor related apoptosis-inducing ligand (TRAIL) has emerged as a promising anticancer agent as it selectively kills cancer cells. However, TRAIL resistance limits its use as a therapeutic agent. An understanding the mechanisms responsible for TRAIL resistance and strategies to overcome it are important...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章,评审

    doi：10.1248/cpb.c15-00732

    authors： Ahmed F,Ishibashi M

    更新日期：2016-01-01 00:00:00

  • Triterpenoid saponins from the seeds of Pharbitis nil.

    abstract：:From the seeds of Pharbitis nil (Convolvulaceae), two new oleanene-type triterpene glycosides, pharbitosides A (1) and B (2), together with beta-sitosterol, beta-sitosterol glucoside (daucosterol), caffeic acid, and methyl caffeate were isolated. The structure of pharbitoside A (1) was elucidated to be queretaroic aci...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.56.203

    authors： Jung DY,Ha H,Lee HY,Kim C,Lee JH,Bae K,Kim JS,Kang SS

    更新日期：2008-02-01 00:00:00

  • Structure-Activity Relationship Study on Col-003, a Protein-Protein Interaction Inhibitor between Collagen and Hsp47.

    abstract：:This study demonstrates the structure-activity relationship of Col-003, a potent collagen-heat-shock protein 47 (Hsp47) interaction inhibitor. Col-003 analogues were successfully synthesized by Pd(0)-catalyzed cross-coupling reactions of 5-bromosalicylaldehyde derivatives with alkyl-metal species, and the inhibitory a...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.c19-00634

    authors： Yoshida M,Saito M,Ito S,Ogawa K,Goshima N,Nagata K,Doi T

    更新日期：2020-03-01 00:00:00

  • Synthetic studies on (+)-biotin, part 15: A chiral squaramide-mediated enantioselective alcoholysis approach toward the total synthesis of (+)-biotin.

    abstract：:An efficient stereocontrolled total synthesis of (+)-biotin (1) has been achieved via the intermediacy of Roche's lactone 5 starting from cis-1,3-dibenzyl-2-imidazole-4,5-dicarboxylic acid (2). The bifunctional cinchona alkaloid-derived squaramide-promoted enantioselective alcoholysis was utilizing as a tool for the c...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.59.488

    authors： Chen XX,Xiong F,Fu H,Liu ZQ,Chen FE

    更新日期：2011-01-01 00:00:00

  • Further studies on new furostanol saponins from the bulbs of Allium macrostemon.

    abstract：:Further studies by means of preparative HPLC led to the isolation of two new furostanol saponins, macrostemonoside J (1) and L (3), along with an artifact, macrostemonoside K (2) from the bulbs of Allium macrostemon. On the basis of chemical evidence and spectral analysis (1H-, 13C-NMR and FAB-MS), the structure of 1 ...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.42.2180

    authors： Peng J,Yao X,Okada Y,Okuyama T

    更新日期：1994-10-01 00:00:00

  • Cathodic adsorptive stripping square-wave voltammetry of the anti-inflammatory drug meloxicam.

    abstract：:The adsorptive behavior of the anti-inflammatory drug meloxicam was studied by cyclic, differentia-pulse and square-wave voltammetry on a hanging mercury drop electrode (HMDE). The drug was accumulated at HMDE and a well-defined stripping peak current was obtained at -1.42 V vs. Ag/AgCl (saturated KCl) electrode in ac...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.49.1257

    authors： Radi AE,Ghoneim M,Beltagi A

    更新日期：2001-10-01 00:00:00

  • Synthesis of (±)-8-deisopropyladunctin B.

    abstract：:(±)-8-Deisopropyladunctin B, the deisopropyl form of adunctin B, which was isolated from the leaves of Piper aduncum (Piperaceae) collected in Papua New Guinea, was synthesized in 0.77% overall yield in 17 steps from 5,7-dimethoxycoumarin-3-carboxylate. The key step was our original stereoconvergent skeleton transform...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.60.94

    authors： Nomura S,Arimitsu K,Yamaguchi S,Kosuga Y,Kakimoto Y,Komai T,Hasegawa K,Nakanishi A,Miyoshi T,Iwasaki H,Ozeki M,Kawasaki I,Kurume A,Ohta S,Yamashita M

    更新日期：2012-01-01 00:00:00

  • Enzymatic generation of alloxan radicals in rat liver microsomes: possible participation of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-cytochrome P-450 reductase.

    abstract：:Electron spin resonance studies showed that addition of rat liver microsomes to the reaction system of alloxan with reduced nicotinamide adenine dinucleotide phosphate (NADPH) resulted in a marked increase in the generation of alloxan radicals (AH.), whereas heat-denatured microsomes were without such effect. Oxidatio...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.40.432

    authors： Sakurai K,Haga K,Ogiso T

    更新日期：1992-02-01 00:00:00

  • Three new naphthoquinone derivatives from Diospyros maritima Blume.

    abstract：:Three new naphthoquinone derivatives, 6-(1-ethoxyethyl)plumbagin (16), ethylidene-3,3'-biplumbagin (17), and ethylidene-3,6'-biplumbagin (18), were isolated, in addition to six known naphthoquinones, isozeylanone (10), 3,3'-biplumbagin (11), chitranone (12), methylene-3,3'-biplumbagin (13), 2,3-epoxyplumbagin (14), an...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.50.590

    authors： Higa M,Noha N,Yokaryo H,Ogihara K,Yogi S

    更新日期：2002-05-01 00:00:00

  • Spray freeze-dried porous microparticles of a poorly water-soluble drug for respiratory delivery.

    abstract：:Particles of poorly water-soluble drugs were prepared to develop a dry powder inhaler (DPI). Spray freeze-drying (SFD) technique using a four-fluid nozzle (4N), which has been developed by authors, was applied in this research. Ciclosporin and mannitol were used as a poorly water-soluble model drug and a dissolution-e...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.c12-00208

    authors： Niwa T,Mizutani D,Danjo K

    更新日期：2012-01-01 00:00:00

  • An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes.

    abstract：:Enantiomerically pure (1S,3S)- and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanes have been efficiently synthesized from L-aspartic acid. The title compounds are isosteres of ribose and may be used to construct nucleoside analogs with important antiviral and antineoplastic activities as demonstrated by a concise total...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.51.1153

    authors： Rapoport H,Chen Y,Mohareb RM,Ahn JH,Sim TB,Ho JZ

    更新日期：2003-10-01 00:00:00

  • Structure-based design and synthesis of fluorescent PPARalpha/delta co-agonist and its application as a probe for fluorescent polarization assay of PPARdelta ligands.

    abstract：:Based on the result of X-ray crystallographic analysis of our peroxisome proliferator-activated receptor alpha and delta (PPARalpha/delta) co-agonist complexed with human PPAR ligand binding domain (LBD), we designed and synthesized an optically active fluorescent PPARalpha/delta co-agonist, which has a pyrene unit in...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.56.1357

    authors： Araya Y,Kasuga J,Toyota K,Hirakawa Y,Oyama T,Makishima M,Morikawa K,Hashimoto Y,Miyachi H

    更新日期：2008-09-01 00:00:00

  • Steroidal glycosides from the underground parts of Solanum sodomaeum.

    abstract：:A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addit...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.54.230

    authors： Ono M,Nishimura K,Suzuki K,Fukushima T,Igoshi K,Yoshimitsu H,Ikeda T,Nohara T

    更新日期：2006-02-01 00:00:00

  • Synthesis and structure-activity studies of a series of 1-oxa-8-azaspiro[4.5]decanes as M1 muscarinic agonists.

    abstract：:2,8-Dimethyl-1-oxa-8-azaspiro[4,5]decan-3-one (17), designed by incorporating the tetrahydrofuran ring moiety of muscarone into an 8-azaspiro[4,5]decane skeleton, and related 1-oxa-8-azaspiro[4.5]decanes were synthesized and assessed as M1 muscarinic agonists for the symptomatic treatment of dementia of Alzheimer's ty...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.43.842

    authors： Tsukamoto S,Fujii M,Yasunaga T,Matsuda K,Wanibuchi F,Hidaka K,Furuya T,Tamura T

    更新日期：1995-05-01 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

  • Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis.

    abstract：:Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione c...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.59.1285

    authors： Thanigaimalai P,Lee KC,Sharma VK,Sharma N,Roh E,Kim Y,Jung SH

    更新日期：2011-01-01 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

  • Development and application of spectrophotometric methods for the determination of citalopram hydrobromide in dosage forms.

    abstract：:Study was carried out to develop two simple, fast, accurate and sensitive spectrophotometric methods (A and B) for the determination of citalopram hydrobromide in commercial tablet formulations. In method A, UV spectrophotometer determined the contents of citalopram hydrobromide in tablets at 240 nm in methanol solven...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.54.432

    authors： Raza A

    更新日期：2006-04-01 00:00:00

  • Sesquiterpenes from Ainsliaea fragrans and their inhibitory activities against cyclooxygenases-1 and 2.

    abstract：:One new guaiane-type sesquiterpene glycoside, 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C (1), was isolated from the whole herb of Ainsliaea fragrans (Compositae), together with five known sesquiterpene lactones: 8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozaluzanin C (2...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.57.597

    authors： Wang H,Wu T,Yan M,Liu G,Li P,Zhang XQ,Ye WC,Zhang LY

    更新日期：2009-06-01 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

  • Stereochemistry of new nitrogen containing heterocyclic aldehyde. VII. Potentiometric, conductometric and thermodynamic studies of novel quinoline azodyes and their metal complexes with some transition metals.

    abstract：:A novel series of quinoline azodyes (5-(4'-derivatives phenyldiazo)-8-hydroxy-7-quinolinecarboxaldehyde)) (HL1-HL5) has been prepared and characterized by elemental analyses, 1H-NMR and IR spectra. The IR spectral data indicate that the compounds can exist in two resonance structures. Proton-ligand dissociation consta...

    journal_title：Chemical & pharmaceutical bulletin

    pub_type： 杂志文章

    doi：10.1248/cpb.49.1308

    authors： El-Sonbati AZ,El-Bindary AA,Shoair AGF,Younes RM

    更新日期：2001-10-01 00:00:00