Antiviral agents. I. Analogs and derivatives of 2-diethylaminoethyl 4-methylpiperazine-1-carboxylate

Angier, Robert B.; Murdock, K. C.; Curran, William V.; Sollenberger, Paula Y.; Casey, Jeremiah P.

doi:10.1021/jm00310a019

Cited by 7 publications

(2 citation statements)

References 3 publications

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“…N , N- 4-Trimethyl-1-piperazinecarboxamide, 3iii. , The pure urea derivative was collected at 120−122 °C as a pale yellow oil (1−2 mmHg) following method A, in 87.4% yield (74.7 g). IR (BaF 2 ): 2936−2791 (Sp, H), 1650 (CO) cm -1 .…”

Section: Methodsmentioning

confidence: 99%

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis¹

El‐Faham

Alberício

2008

J. Org. Chem.

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Here we describe a new family of N-form immonium-type coupling reagents that differ in their carbocation skeleton structure. The N-methylpiperazine derivative failed to form immonium salts, while the thiomorpholine derivative did not give better results than the coupling reagents currently used. The presence of the morpholine had a marked influence on the solubility and stability as well as the reactivity of the reagent. Finally, the fluoroamidinium salt performed extremely well in the presence of only 1 equiv of base, thereby confirming the effect of the proton acceptor in the reaction.

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Section: Methodsmentioning

confidence: 99%

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis¹

El‐Faham

Alberício

2008

J. Org. Chem.

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“…Sodium 1-[4-(Ethoxycarbonyl)-1,4-diazacycloheptan-1-yl]diazen-1-ium-1,2-diolate (JS-35 - 167). A solution of 4 g (0.023 mol) of 1-ethoxycarbonyl-1,4-diazacycloheptane in 4.6 mL of 30% methanolic sodium methoxide, 5 mL of methanol, and 15 mL of ether was placed in a Parr bottle. The homogeneous solution was purged with nitrogen, charged with 50 psi of nitric oxide, and stirred at room temperature overnight.…”

Section: Methodsmentioning

confidence: 99%

Antitumor Activity of JS-K [O²-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and Related O²-Aryl Diazeniumdiolates in Vitro and in Vivo

Saavedra²,

et al. 2006

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The literature provides evidence that metabolic nitric oxide (NO) release mediates the cytotoxic activities (against human leukemia and prostate cancer xenografts in mice) of JS-K, a compound of structure R(2)N-N(O)=NO-Ar for which R(2)N is 4-(ethoxycarbonyl)piperazin-1-yl and Ar is 2,4-dinitrophenyl. Here we present comparative data on the potencies of JS-K and 41 other O(2)-arylated diazeniumdiolates as inhibitors of HL-60 human leukemia cell proliferation, as well as in the NCI 51-cell-line screen for six of them. The data show JS-K to be the most potent of the 42 in both screens and suggest that other features of its structure and metabolism besides NO release may contribute importantly to its activity. Results with control compounds implicate JS-K's arylating ability, and the surprisingly low IC(50) value of the N-(ethoxycarbonyl)piperazine byproduct of NO release suggests a role for the R(2)N moiety. In addition to the above-mentioned in vivo activities, JS-K is shown here to be carcinostatic in a rat liver cancer model.

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Use of N‐Methylpiperazine for the Preparation of Piperazine‐Based Unsymmetrical Bis‐Ureas as Anti‐HIV Agents

et al. 2008

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Antiviral agents. I. Analogs and derivatives of 2-diethylaminoethyl 4-methylpiperazine-1-carboxylate

Cited by 7 publications

References 3 publications

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis¹

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis¹

Antitumor Activity of JS-K [O²-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and Related O²-Aryl Diazeniumdiolates in Vitro and in Vivo

Use of N‐Methylpiperazine for the Preparation of Piperazine‐Based Unsymmetrical Bis‐Ureas as Anti‐HIV Agents

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Antiviral agents. I. Analogs and derivatives of 2-diethylaminoethyl 4-methylpiperazine-1-carboxylate

Cited by 7 publications

References 3 publications

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis1

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis1

Antitumor Activity of JS-K [O2-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and Related O2-Aryl Diazeniumdiolates in Vitro and in Vivo

Use of N‐Methylpiperazine for the Preparation of Piperazine‐Based Unsymmetrical Bis‐Ureas as Anti‐HIV Agents

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Product

Resources

About

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis¹

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis¹

Antitumor Activity of JS-K [O²-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and Related O²-Aryl Diazeniumdiolates in Vitro and in Vivo