Cyanuric Chloride Derivatives. II. Substituted Melamines

Kaiser, Donald W.; Thurston, Jack T.; Dudley, James R.; Schaefer, Frederic C.; Hechenbleikner, Ingenuin; Holm-Hansen, Dagfrid

doi:10.1021/ja01151a002

Cited by 96 publications

(25 citation statements)

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“…This is a feasible approach because the reactivity of the chlorine atoms in ADCT is much higher than the chlorine atom in ACHT in alkali‐catalyzed hydrolysis reactions 26. It has been well established that because of the strong electron‐withdrawing effect of the triazine ring, the CCl groups in ADCT and ACHT are not ordinary alkyl halides; instead, they behave more like acid chlorides 27–29. In ACHT, both the nitrogen atom and the oxygen atom share their lone pair of electrons with the conjugated ring structure.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial polymers containing melamine derivatives. I. Preparation and characterization of chloromelamine‐based cellulose

Braun

Sun

2004

J. Polym. Sci. A Polym. Chem.

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A reactive melamine derivative, 2‐amino‐4‐chloro‐6‐hydroxy‐s‐triazine (ACHT), was synthesized through the controlled hydrolysis of 2‐amino‐4,6‐dichloro‐s‐triazine. The reaction was characterized with Fourier transform infrared study and elemental analysis. ACHT could react with cotton cellulose at room temperature with a cold‐pad‐batch treatment process. Upon chlorination reactions, the amino group of covalently bound ACHT could be transformed into an N‐halamine structure, providing potent, durable, and rechargeable antimicrobial activities against both gram‐negative and gram‐positive bacteria. The chlorination mechanism and the structure–property relationship of the treated samples were further examined. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3818–3827, 2004

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Section: Resultsmentioning

confidence: 99%

Antimicrobial polymers containing melamine derivatives. I. Preparation and characterization of chloromelamine‐based cellulose

Braun

Sun

2004

J. Polym. Sci. A Polym. Chem.

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“…Trishexylaminomelamine (THAM) was synthesized according to the method of Kaiser et al (18). Cyanuric chloride (TCI America, Tokyo, Japan) was reacted with a 3.3 molar ratio of N-BOC-1,6-diaminohexane (Alfa Aesar, Ward Hill, MA) in refluxing water for 1.25 h. The pH of the solution was monitored with phenolphthalein, and the pink color was maintained by gradual addition of a 0.4 M sodium carbonate solution.…”

Section: Methodsmentioning

confidence: 99%

Novel Compounds Containing Multiple Guanide Groups That Bind the HIV Coreceptor CXCR4

Wilkinson

Pincus

Shepard

et al. 2011

Antimicrob Agents Chemother

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The G-protein-coupled receptor CXCR4 acts as a coreceptor for human immunodeficiency virus type 1 (HIV-1) infection, as well as being involved in signaling cell migration and proliferation. Compounds that block CXCR4 interactions have potential uses as HIV entry inhibitors to complement drugs such as maraviroc that block the alternate coreceptor CCR5 or in cancer therapy. The peptide T140, which contains five arginine residues, is the most potent antagonist of CXCR4 developed to date. In a search for nonpeptide CXCR4 ligands that could inhibit HIV entry, three series of compounds were synthesized from 12 linear and branched polyamines with 2, 3, 4, 6, or 8 amino groups, which were substituted to produce the corresponding guanidines, biguanides, or phenylguanides. The resulting compounds were tested for their ability to compete with T140 for binding to the human CXCR4 receptor expressed on mammalian cells. The most effective compounds bound CXCR4 with a 50% inhibitory concentration of 200 nM, and all of the compounds had very low cytotoxicity. Two series of compounds were then tested for their ability to inhibit the infection of TZM-bl cells with X4 and R5 strains of HIV-1. Spermine phenylguanide and spermidine phenylguanide inhibited infection by X4 strains, but not by R5 strains, at low micromolar concentrations. These results support further investigation and development of these compounds as HIV entry inhibitors.

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“…2‐[ N , N ‐Bis(2‐hydroxyethyl)amine]‐4,6‐dimethoxy‐1,3,5‐triazine (modifier A ) and 2,4‐bis[ N , N ‐bis(2‐hydroxyethyl)amine]‐6‐methoxy‐1,3,5‐triazine (modifier B ) had melting points of 116.7–117.2 and 104.2–104.7 °C, respectively, whereas 2,4,6‐tris[ N , N ‐bis(2‐hydroxyethyl)amine]‐1,3,5‐triazine (modifier C ) melted at a somewhat higher temperature of T m,found = 168.4–168.7 °C, T m,lit. = 169–170 °C 16…”

Section: Resultsmentioning

confidence: 99%

Amine Modifiers with an s‐Triazine Ring for Unsaturated Polyester Resins, 1

Duliban

2006

Macro Materials & Eng

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Summary: Synthesis and properties of amine modifiers for unsaturated polyester resins are presented. The modifiers were obtained by reacting 3‐azapentan‐1,5‐diol (diethanoloamine) with 2,4‐dichloro‐6‐methoxy‐1,3,5‐triazine, 2‐chloro‐4,6‐dimethoxy‐1,3,5‐triazine or with cyanuric chloride. They were incorporated into the structure of typical unsaturated polyester resins in the polycondensation stage, i.e. prior to dilution with styrene, in the amount of 0.25 through to 2.0 wt.‐%. The effect of the modifier presence on the curing behavior of the resulting resins is discussed.Gelation times for unsaturated polyester resins modified with modifiers A, B, and C are shown with the curing system consisting of peroxide initiator and (▪): 0.10 cm3, (•): 0.15 cm3, (▴): 0.25 cm3, and (▾): 0.50 cm3 of cobalt(II) octenate solution per 25 g of resin.imageGelation times for unsaturated polyester resins modified with modifiers A, B, and C are shown with the curing system consisting of peroxide initiator and (▪): 0.10 cm3, (•): 0.15 cm3, (▴): 0.25 cm3, and (▾): 0.50 cm3 of cobalt(II) octenate solution per 25 g of resin.

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Cyanuric Chloride Derivatives. II. Substituted Melamines

Cited by 96 publications

References 0 publications

Antimicrobial polymers containing melamine derivatives. I. Preparation and characterization of chloromelamine‐based cellulose

Antimicrobial polymers containing melamine derivatives. I. Preparation and characterization of chloromelamine‐based cellulose

Novel Compounds Containing Multiple Guanide Groups That Bind the HIV Coreceptor CXCR4

Amine Modifiers with an s‐Triazine Ring for Unsaturated Polyester Resins, 1

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