Molecules

9 pages, 74 KB

Open AccessArticle

Synthesis and Anticancer Activities of Novel 1,4-Disubstituted Phthalazines

by Juan Li, Yan-Fang Zhao, Xiao-Ye Yuan, Jing-Xiong Xu and Ping Gong^*

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, 110016 Shenyang, Liaoning, P. R. China

Molecules 2006, 11(7), 574-582; https://doi.org/10.3390/11070574 - 27 Jul 2006

Cited by 167 | Viewed by 14495

Abstract

A series of novel 1-anilino-4-(arylsulfanylmethyl)phthalazines were designed and synthesized. The structures of all the compounds were confirmed by IR, 1H-NMR, elemental analysis and MS. The analogues 1-(3-chloro-4-fluoroanilino)-4-(3,4- difluorophenylthio-methyl)phthalazine (12) and 1-(4-fluoro-3-trifluoromethylanilino)-4- (3,4-difluorophenyl-thiomethyl)phthalazine (13) showed higher activity than a cisplatin control when tested in [...] Read more.

A series of novel 1-anilino-4-(arylsulfanylmethyl)phthalazines were designed and synthesized. The structures of all the compounds were confirmed by IR, 1H-NMR, elemental analysis and MS. The analogues 1-(3-chloro-4-fluoroanilino)-4-(3,4- difluorophenylthio-methyl)phthalazine (12) and 1-(4-fluoro-3-trifluoromethylanilino)-4- (3,4-difluorophenyl-thiomethyl)phthalazine (13) showed higher activity than a cisplatin control when tested in vitro against two different cancer cell lines using the microculture tetrazolium method (MTT) method. Full article

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10 pages, 113 KB

Open AccessArticle

Novel Furanoid α-Substitued α-Amino Acid as a Potent Turn Mimic in Peptide Synthesis

by Miroslava Martinková^*, Jozef Gonda and Jana Raschmanová

Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, SK-040 01 Košice, Slovak Republic

Molecules 2006, 11(7), 564-573; https://doi.org/10.3390/11070564 - 26 Jul 2006

Cited by 24 | Viewed by 8895

Abstract

A stereoselective approach has been developed to the new sugar amino acid and potential potent turn mimic 5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O- isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose 3-C-carboxylic acid (12), via the [3,3]-sigmatropic rearrangement of allylic thiocyanates (Z)-6 and (E)-7, prepared from D-xylose. The synthesis of a new dipeptide 13 is [...] Read more.

A stereoselective approach has been developed to the new sugar amino acid and potential potent turn mimic 5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O- isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose 3-C-carboxylic acid (12), via the [3,3]-sigmatropic rearrangement of allylic thiocyanates (Z)-6 and (E)-7, prepared from D-xylose. The synthesis of a new dipeptide 13 is also described. Full article

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8 pages, 56 KB

Open AccessArticle

Novel Reaction of N,N'-Bisarylmethanediamines with Formaldehyde. Synthesis of Some New 1,3,5-Triaryl-1,3,5-hexahydrotriazines

by Mehdi Ghandi^*, Farshid Salimi and Abolfazl Olyaei

School of Chemistry, University College of Science, University of Tehran, Tehran, Iran

Molecules 2006, 11(7), 556-563; https://doi.org/10.3390/11070556 - 26 Jul 2006

Cited by 13 | Viewed by 11825

Abstract

The acid-catalyzed cyclocondensation of N,N'-bisaryl (aryl = 2-pyrimidinyl, 2- pyrazinyl and 4-nitrophenyl) methanediamines 5a-c with aqueous formaldehyde in refluxing acetonitrile leads to the formation of the corresponding 1,3,5-triaryl-1,3,5-hexa- hydrotriazines 6a-c. The stoichiometric reactions of 2-aminopyrimidine and 2-amino- pyrazine with aqueous formaldehyde in acetonitrile [...] Read more.

The acid-catalyzed cyclocondensation of N,N'-bisaryl (aryl = 2-pyrimidinyl, 2- pyrazinyl and 4-nitrophenyl) methanediamines 5a-c with aqueous formaldehyde in refluxing acetonitrile leads to the formation of the corresponding 1,3,5-triaryl-1,3,5-hexa- hydrotriazines 6a-c. The stoichiometric reactions of 2-aminopyrimidine and 2-amino- pyrazine with aqueous formaldehyde in acetonitrile under reflux conditions also afforded 6a and 6b, respectively. Treatment of 2-aminopyrimidine with aqueous formaldehyde in a 3:2 ratio yielded N,N',N"-tris(2-pyrimidinyl)dimethylenetriamine (7a) as a sole product, which upon subsequent reaction with formaldehyde also afforded 6a. The reaction of N,N'-biphenylmethanediamine with formaldehyde was also investigated. Full article

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7 pages, 62 KB

Open AccessArticle

Chemical Composition and Antimicrobial Activity of the Essential Oil from Ambrosia trifida L.

by Peng Wang^1,2, Chui Hua Kong^1,* and Chao Xian Zhang³

¹ Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang 110016, P.R. China

² Graduate School, Chinese Academy of Sciences, Beijing 100039, P.R. ChinaGraduate School, Chinese Academy of Sciences, Beijing 100039, P.R. China

³ Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100094, P.R. China

Molecules 2006, 11(7), 549-555; https://doi.org/10.3390/11070549 - 25 Jul 2006

Cited by 36 | Viewed by 11610

Abstract

The essential oil obtained by steam distillation of dried aerial parts of Ambrosia trifida L. from Northeast China was analyzed by GC and GC–MS. The essential oil yield based on dried plant material was 0.12% and thirty-five compounds (corresponding to 86.7% of the [...] Read more.

The essential oil obtained by steam distillation of dried aerial parts of Ambrosia trifida L. from Northeast China was analyzed by GC and GC–MS. The essential oil yield based on dried plant material was 0.12% and thirty-five compounds (corresponding to 86.7% of the total weight) were identified. The main components were: bornyl acetate (15.5%), borneol (8.5%), caryophyllene oxide (8.3%), α-pinene (8.0%), germacrene D (6.3%), β-caryophyllene (4.6%), trans-carveol (2.9%), β-myrcene (2.6%), camphor (2.4%) and limonene (3.2%). A. trifida essential oil demonstrated bactericidal and fungicidal activity against six bacterial strains and two fungal strains, using the agar diffusion method. Full article

10 pages, 119 KB

Open AccessArticle

A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae

by Kunimitsu Kaya^1,*, Louise F. Morrison², Geoffrey A. Codd^2,*, James S. Metcalf², Tomoharu Sano³, Hiroo Takagi³ and Takuya Kubo¹

¹ Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan

² Division of Environmental and Applied Biology, School of Life Sciences, University of Dundee, Dundee DD1 4HN, UK

³ National Institute for Environmental Studies, 16-2 Onogawa, Tsukuba Ibaraki 305-8506, Japan

Molecules 2006, 11(7), 539-548; https://doi.org/10.3390/11070539 - 22 Jul 2006

Cited by 13 | Viewed by 10429

Abstract

A novel biosurfactant, 2-acyloxyethylphosphonate, was isolated from waterblooms of Aphanizomenon flos-aquae. Its structure was elucidated by chemical degradation and HRFABMS, GC/EI-MS and 1D- and 2D-NMR spectral analyses. The surfactant contained one mole of 2-hydroxyethylphosphonate and one mole of fatty acid, with hexadecanoic acid [...] Read more.

A novel biosurfactant, 2-acyloxyethylphosphonate, was isolated from waterblooms of Aphanizomenon flos-aquae. Its structure was elucidated by chemical degradation and HRFABMS, GC/EI-MS and 1D- and 2D-NMR spectral analyses. The surfactant contained one mole of 2-hydroxyethylphosphonate and one mole of fatty acid, with hexadecanoic acid accounting for 84.1% of the total fatty acid content. The structure was confirmed by synthesis of 2-oleoyloxyethylphosphonate from ethylene oxide, phosphorus acid and oleic acid chloride. Considering the isolated surfactant molecule as hexadecanoyloxyethylphosphonic acid (mw. 364), the critical micelle concentration (CMC) was about 22 mM. Full article

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11 pages, 384 KB

Open AccessArticle

Synthesis and Structure of a Sodium Complex of an Aromatic β-Diketone and Pyrazolylpyridine

by Ana C. Coelho¹, Filipe A. Almeida Paz¹, Jacek Klinowski², Martyn Pillinger¹ and Isabel S. Gonçalves^1,*

¹ Department of Chemistry, CICECO, University of Aveiro, 3810-193 Aveiro, Portugal

² Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK

Molecules 2006, 11(7), 528-538; https://doi.org/10.3390/molecules11070528 - 17 Jul 2006

Cited by 6 | Viewed by 10944

Abstract

Reaction of NaH with a THF solution of Eu(BTA)3(pypzH) [BTA = 1-benzoyl-3,3,3-trifluoroacetonate, pypzH = 2-(3-pyrazolyl)pyridine] leads to the formation of theeuropium-free tetrasodium complex [Na₄(pypzH)₂(μ4-BTA)₂(μ2-BTA)₂]. Single-crystal X-ray diffraction studies revealed the presence of a centrosymmetric Na [...] Read more.

Reaction of NaH with a THF solution of Eu(BTA)3(pypzH) [BTA = 1-benzoyl-3,3,3-trifluoroacetonate, pypzH = 2-(3-pyrazolyl)pyridine] leads to the formation of theeuropium-free tetrasodium complex [Na₄(pypzH)₂(μ4-BTA)₂(μ2-BTA)₂]. Single-crystal X-ray diffraction studies revealed the presence of a centrosymmetric Na hybrid tetramer,which fully occupies the contents of the triclinic unit cell. The crystal structure containstwo individual Na cations, Na(1) and Na(2), which have highly irregular {NaN₂O₃} and{NaO₆} local coordination environments, respectively. One of the key features is thepresence of a central {Na₄O₆} core, which is unprecedented for Na . Externally to this{Na₄O₆} cluster pyrazolylpyridine organic molecules are N,N-chelated to Na(1). Eventhough all of the organic residues contain aromatic rings, the crystal packing of individualcentrosymmetric tetrasodium [Na₄(pypzH)₂(μ4-BTA)₂(μ2-BTA)₂] molecular moieties isessentially driven through geometrical aspects combined with weak C–H···π interactions,rather than the expected a priori π-π interactions. The material also contains classicalstrong hydrogen bonds, even though these do not directly contribute to the packingdriving forces. Full article

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5 pages, 62 KB

Open AccessCommunication

[Hydroxy(tosyloxy)iodo]benzene Mediated α-Azidation of Ketones

by Om Prakash^*, Kamaljeet Pannu, Richa Prakash and Anita Batra

Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana, India

Molecules 2006, 11(7), 523-527; https://doi.org/10.3390/11070523 - 14 Jul 2006

Cited by 29 | Viewed by 9530

Abstract

Reaction of various ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment of the α-tosyloxy ketones thus generated in situ with NaN3 offers a one-pot procedure for the synthesis of α-azido ketones. The HTIB used in this conversion may also be generated in situ by [...] Read more.

Reaction of various ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment of the α-tosyloxy ketones thus generated in situ with NaN3 offers a one-pot procedure for the synthesis of α-azido ketones. The HTIB used in this conversion may also be generated in situ by using iodosobenzene in combination with p-toluene- sulphonic acid. Full article

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9 pages, 73 KB

Open AccessArticle

Electrocoagulation of Quinone Pigments

by Neeranuch Chairungsi¹, Kanlaya Jumpatong¹, Patiwat Suebsakwong², Waya Sengpracha³, Weerachai Phutdhawong^2,* and Duang Buddhasukh^1,*

¹ Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

² Department of Chemistry, Faculty of Science, Maejo University, Chiang Mai, 50292, Thailand

³ Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom, 73000, Thailand

Molecules 2006, 11(7), 514-522; https://doi.org/10.3390/11070514 - 14 Jul 2006

Cited by 10 | Viewed by 9620

Abstract

Some representative quinones, viz. one naphthoquinone (plumbagin) and five anthraquinones (alizarin, purpurin, chrysazin, emodin, and anthrarufin), were subjected to electrocoagulation. It was found that the rate and extent of coagulation of these compounds appears to correlate with the number and relative position of [...] Read more.

Some representative quinones, viz. one naphthoquinone (plumbagin) and five anthraquinones (alizarin, purpurin, chrysazin, emodin, and anthrarufin), were subjected to electrocoagulation. It was found that the rate and extent of coagulation of these compounds appears to correlate with the number and relative position of their phenolic substituent groups, and that all of the coagulated quinones could be recovered. Attempts were then made to electrochemically isolate three quinones, namely plumbagin, morindone and erythrolaccin, from natural sources. Full article

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16 pages, 118 KB

Open AccessArticle

Synthesis of Some Thienopyrimidine Derivatives

by Fatma E. M. El-Baih^1,*, Hanan A. S. Al-Blowy¹ and Hassan M. Al-Hazimi²

¹ Women Students-Medical Studies & Sciences Sections, Chemistry Department, College of Science, King Saud University, P.O. Box 22452, Riyadh 11495, Saudi Arabia

² Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

Molecules 2006, 11(7), 498-513; https://doi.org/10.3390/11070498 - 5 Jul 2006

Cited by 38 | Viewed by 14751

Abstract

Thioxothienopyrimidinones, alkylthio- and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolo- pyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents. Full article

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2 pages, 15 KB

Open AccessEditorial

Delayed Open Access or Permanent Non-Open Access

by Shu-Kun Lin

Molecular Diversity Preservation International (MDPI), Matthaeusstrasse 11, Basel CH-4057Switzerland

Molecules 2006, 11(7), 496-497; https://doi.org/10.3390/11070496 - 26 Jun 2006

Cited by 5 | Viewed by 5622

Abstract

Since last year, we have resumed use of a two tier publication system, whereby we have continued to offer full Open Access publication to those authors willing to contribute financially to support this option, while providing authors with the alternative choice of free [...] Read more.

Since last year, we have resumed use of a two tier publication system, whereby we have continued to offer full Open Access publication to those authors willing to contribute financially to support this option, while providing authors with the alternative choice of free publication without Open Access for those who prefer not to pay [1].[...] Full article

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Molecules, Volume 11, Issue 7 (July 2006) – 10 articles , Pages 496-582

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