Biologically Active Stable Radicals; XV<sup>1</sup>. Spin-Labeled Alkyl Carbamate-<i>N</i>-phosphonic Acid Aziridides

N‐Substituted N′‐[6‐methyl‐2‐oxido‐1,3,2‐dioxaphosphinino(5,4,‐b)pyridine‐2‐yl]ureas have been accomplished by condensation of equimolar quantities of chlorides of various carbamidophosphoric acids (3) with 3‐hydroxyl‐6‐methyl‐2‐pyridinemethanol (lutidine diol) (4) in the presence of triethylamine in dry toluene–tetrahydrofuran (1:1) mixture at 45–50°C. Their structures were established by elemental analyses, IR, 1H NMR, 13C NMR, and 31P NMR spectral data. Their antifungal and antibacterial activity is also evaluated. Most of these compounds exhibited moderate antimicrobial activity in the assays. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:509–512, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10181

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“…The synthetic route (Scheme 1) involves the addition reaction of isocyanato phosphonic dichloride (1) [2,3] with various amines (2a-j) at −15…”

Section: Resultsmentioning

confidence: 99%

“…Organophosphorus carbamates demonstrated insecticidal, bactericidal, antiviral, and antitumor activity [1][2][3][4][5]. Industrially they were found to be useful as lubricating oil additives, antioxidants, and polymer stabilizers [6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activity of N‐substituted N′‐[6‐methyl‐2‐oxido‐1,3,2‐dioxaphosphinino(5,4‐b)pyridine‐2‐yl]ureas

Reddy

Venugopal

2003

Heteroatom Chemistry

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“…4 Some diazaphospholes and certain phosphinyl carbamates demonstrated insecticidal, bactericidal, antiviral, antitumor and anticarcinogenic activity. [5][6][7][8][9][10][11][12][13][14][15] As a part of our ongoing programme, aimed at searching for novel antibacterial and antiviral agents with high activity and low toxicity, a synthetic route has been developed to the title compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c] [1,3,2]diazaphosphole-2-oxides

Babu¹,

Kumar²,

Srinivasulu³

et al. 2007

Arkivoc

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Some novel 2-(heterylcarboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo [3,4-c][1,3,2]diazaphosphole-2-oxides (4-13) have been synthesized from reaction of 3,4-diamino-1,2,5-oxadiazole (3) with various dichlorophosphinylcarboxamides (2), which were prepared by C-acylation of electron-rich heterocyclic compounds with dichloro isocyanato phosphine oxide (Kirsanov isocyanate) (1) in dry octane, in the presence of triethylamine at 50-60 °C. Their structures were determined by IR, 1 H, 13 C, 31 P NMR and mass spectral (MS) studies. They were screened for antifungal and antibacterial activity against Curvularia lunata / Aspergillus niger and Staphylococcus aureus / Escherichia coli, respectively. Most of these compounds exhibited moderate activity in the assays.

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“…Organophosphorus compounds containing a benzodiazaphosphole ring have acquired much importance because of their insecticidal, bactericidal, antiviral, and anticarcinogenic properties [2][3][4]. The search for a satisfactory drug for cancer also produced many new phosphorus heterocyclic compounds [5,6], and many of them possessed significant antitumor activity [6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐substituted‐2,3‐dihydro‐5‐benzoyl‐1H‐1,3,2‐benzodiazaphosphole 2‐oxides/sulfides

Reddy

Babu

Reddy

et al. 2002

Heteroatom Chemistry

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Syntheses of 2-aryloxy/2-chloro ethoxy- 2, 3-dihydro-5-benzoyl-1H-1, 3, 2-benzodiaza-phosphole 2-oxides 3a-h were accomplished by reactions of equimolar quantities of 3,4-diaminobenzophenone (1) with various aryl/chloroethoxy phosphorodichloridates 2a-g and 2h in the presence of triethylamine at 50-60• C. Compounds 3i-k were prepared by reacting 3,4-diaminobenzophenone (1) with aryl thiophosphorodichloridates 2i-k under similar conditions. They were characterized by IR,

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Biologically Active Stable Radicals; XV¹. Spin-Labeled Alkyl Carbamate-N-phosphonic Acid Aziridides

Cited by 20 publications

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Synthesis and antimicrobial activity of N‐substituted N′‐[6‐methyl‐2‐oxido‐1,3,2‐dioxaphosphinino(5,4‐b)pyridine‐2‐yl]ureas

Synthesis and antimicrobial activity of N‐substituted N′‐[6‐methyl‐2‐oxido‐1,3,2‐dioxaphosphinino(5,4‐b)pyridine‐2‐yl]ureas

Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c] [1,3,2]diazaphosphole-2-oxides

Synthesis of 2‐substituted‐2,3‐dihydro‐5‐benzoyl‐1H‐1,3,2‐benzodiazaphosphole 2‐oxides/sulfides

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Biologically Active Stable Radicals; XV1. Spin-Labeled Alkyl Carbamate-N-phosphonic Acid Aziridides

Cited by 20 publications

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Synthesis and antimicrobial activity of N‐substituted N′‐[6‐methyl‐2‐oxido‐1,3,2‐dioxaphosphinino(5,4‐b)pyridine‐2‐yl]ureas

Synthesis and antimicrobial activity of N‐substituted N′‐[6‐methyl‐2‐oxido‐1,3,2‐dioxaphosphinino(5,4‐b)pyridine‐2‐yl]ureas

Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c] [1,3,2]diazaphosphole-2-oxides

Synthesis of 2‐substituted‐2,3‐dihydro‐5‐benzoyl‐1H‐1,3,2‐benzodiazaphosphole 2‐oxides/sulfides

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Biologically Active Stable Radicals; XV¹. Spin-Labeled Alkyl Carbamate-N-phosphonic Acid Aziridides