- Synthesis, crystal structure, biological evaluation, electronic aspects of hydrogen bonds, and QSAR studies of some new N-(substituted phenylurea) diazaphosphore derivatives as anticancer agents
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A new series of 2-[N-(R-phenylureido)]-1,3,2-diazaphosphore-2-oxide derivatives (R = CH3, F, NO2, CN) were synthesized and characterized by 31P, 1H, 13C NMR and FT-IR spectral techniques. All the compounds were evaluated for their antibacterial activity against some Gram-positive, Gram-negative strains of bacteria, as well as for their cytotoxic effects on MCF-7, MDA-MB-231, PC-3, HeLa, and K562 human cell lines. In vitro activity results exhibited an important role for six-membered diaza ring in both assays as well as high effect of meta-methyl and ortho-fluoro substitutes on the aromatic ring against the studied human cell lines and B. subtilis bacteria, respectively. To understand the correlation between the anticancer activity and physicochemical properties of the synthesized compounds, the QSAR studies were carried out. Further, the crystal structure of compound 15 was investigated and revealed that the title derivative is composed of two symmetrically independent molecules in the solid state with anti configuration the C=O versus P=O. NBO and AIM analyses were performed to investigate electronic aspects of hydrogen bonding of the crystal cluster, which play an extremely important role in biochemical systems.
- Dorosti, Niloufar,Delfan, Bahram,Gholivand, Khodayar,Ebrahimi Valmoozi, Ali Asghar
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- Synthesis and antimicrobial activity of some new N-(substituted phenyl)-N′-[2,3-dihydro-2-oxido-3-(4′-fluorophenyl)-1H-(1,3,2) benzoxazaphosphorin 2-yl]ureas
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(Chemical Equation Presented) Substituted benzoxazaphosphorin 2-yl ureas were synthesized by reacting 2-(4-fluoro-phenylamino)-methylphenol (4) with different carbamidophosphoric acid dichlorides (3) in the presence of triethylamine in dry toluene at 45-50°C and characterized by spectral data. These compounds were found to possess good antimicrobial activity.
- Haranath,Sreedhar Kumar,Suresh Reddy,Naga Raju,Devendranath Reddy
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- Synthesis and antimicrobial activity of 1-[(substituted carbamoyl)amino]-1H,3H-1λ5-[1,3,2]oxazaphospholo[3,4-a] benzimidazol-1-ones
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1-[(Substituted carbamoyl)amino]-1H,3H-1λ5-[1,3,2]oxazaphospholo[3, 4-a]benzimidazol-1-ones were synthesized by reacting benzimidazole 2-methanol (4) with different chlorides of carbamidophosphoric acids (3) in the presence of triethylamine at 40-45°C. Th
- Anasuyamma,Haranath,Kumar, M. Anil,Reddy, C. Suresh,Raju, C. Naga
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- Synthesis of N-(Substituted)-N′-[5,5′-bis(bromomethyl)-2-oxido- 1,3,2-dioxaphosphorinane-2yl] ureas
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Synthesis of N-(Substituted)-N′-[5,5′bis(bromomethyl)-2-oxido- 1,3,2-dioxaphosphorinane-2yl] ureas has been accomplished by condensation of equimolar quantities of chlorides of various carbamidophosphoric acids 3 with 2,2′-bis(bromomethyl)l,3-propanediol
- Stephen Babu,Kiran,Ananda Kumar,Devendranath Reddy,Suresh Reddy
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- Synthesis of N-(substituted aryl/cyclohexyl)-N′-[5-bromo-5-nitro-2-oxido-1,3, 2-dioxaphosphorinane-2-yl]ureas
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N-(Substituted aryl/cyclohexyl)-N′-[5-bromo-5-nitro-2-oxido-1,3, 2-dioxaphosphorinane-2-yl]ureas RR′P(O)NHC(O)NHR" (5) were synthesized by the reactions of 2-bromo-2-nitro-1,3-propanediol (4) with chlorides of aryl/cyclohexyl carbamidophosphoric acids (3) in the presence of triethylamine at room temperature. Their ir, 1H, 13C and 31P nmr spectral data are discussed.
- Govardhana Reddy, P. Vasu,Hari Babu,Suresh Reddy
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- Synthesis and antimicrobial activity of N-(substituted)-n′-[8-oxido dinaphtho-16h-2,1-z:(1′,2′-g)1,3,2-dioxaphosphocin-8-yl]ureas
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Substituted dinaphtho-16H-(2,1-d:(1′,2′-g)1,3,2- dioxaphosphocin-8-yl]ureas (5a-i) were synthesized by reacting bis (2-hydroxy-1-naphthyl)methane (4) with different carbamidophosphoric acid dichlorides (3) in the presence of triethylamine in dry toluene a
- Anasuyamma,Haranath,Kumar, B. Siva,Reddy, C. Suresh
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p. 147 - 154
(2008/02/12)
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- Synthesis and antimicrobial activity of N-(substituted)-N′-[1,2,4, 8,10,11-hexachloro-6-oxido-12H-dibenzo(d,g)(1,3,2)-dioxaphosphocin-6-yl]ureas
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Substituted dibenzo dioxaphosphocin-6-yl ureas were synthesized by reacting hexachlorophene (4) with different carbamidophosphoric acid dichlorides (3) in the presence of triethylamine in dry toluene at 45-50 °C. Their IR, 1H, 13C and 31P NMR spectral data is discussed. These compounds were found to possess good antimicrobial activity.
- Haranath,Anasuyamma,Vasu Govardhana Reddy,Suresh Reddy
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p. 1001 - 1004
(2007/10/03)
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- Synthesis and antimicrobial activity of N-substituted N′-[6-methyl-2-oxido-1,3,2-dioxaphosphinino(5,4-b)pyride-2-yl]ureas
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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.
- Reddy, P. Vasu Govardhana,Reddy, C. Suresh,Venugopal
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p. 509 - 512
(2007/10/03)
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- Synthesis and antimicrobial activity of N-(substituted)-N'-(2,3-dihydro-2-oxido-5-benzoyl-1H-1,3,2-benzodiazaphosphol-2-yl) ureas.
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N-(substituted)-N'-(2,3-dihydro-5-benzoyl-2-oxido-1H-1,3,2-benzodiazaphosphol-2-yl) ureas were synthesized by reacting 3,4-diaminobenzophenone (4) with different chlorides of carbamidophosphoric acids (3) in the presence of triethylamine at 40-45 degrees C. Their 1H-, 13C- and 31P-NMR spectral data are discussed. The title compounds were screened for antifungal and antibacterial activity against the fungi Aspergillus niger and Fusarium solani and bacteria Escherichia coli and Staphylococcus aureus. These compounds showed higher antibacterial activity when compared with antifungal activity.
- Vasu Govardhana Reddy, Peddaiahgari,Suresh Reddy, Cirandur,Naga Raju, Chamarthi
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p. 860 - 863
(2007/10/03)
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- Synthesis and antimicrobial activity of N-(substitutedphenyl)-N'-[1,2,3,4-tetrahydro-2-oxido- 1,3,2-benzodiazaphosphorine-2-y1] ureas
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N-(Substitutedphenyl)-N′-[1,2,3,4-tetrahydro-2-oxido- 1,3,2-benzodiazaphosphorine-2-y1] ureas 5 which are substituted ureas of the type RR′P(O)NHC(O)NR″R? have been synthesized from reactions of 2-aminobenzylamine 2 with chlorides of arylcarbamidophosphor
- Nagaprasada Rao,Reddy,Reddy
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p. 817 - 821
(2007/10/03)
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- Synthesis and antimicrobial activity of 2-substituted-2,3-dihydro-1H-naphtho- [1,8-de]- 1,3,2-diazaphosphorine 2-oxides/sulfides
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Several 2-alkylcarbamato/thiocarbamato/arylcarbamido/trichloromethyl/bis(2-chloro- ethyl)amino/chloroethoxy/ aryloxy-2.3-dihydro-1H-naphtho-[1,8-de]-1,3,2-diazaphosphorine 2-oxides/sulfides (4 and 6) are synthesized by reacting equimolar quantities of 1,8-diamino-naphthalene 1 with various dichlorophosphinyl carbamates/thiocarbamates/arylcarbamides 3a-1, trichloromethylphosphonic dichloride 5a, bis(2-chloroethyl)phosphoramidic dichloride 5b, O-2-chloroethyl phosphoryl chloride 5c and arylphosphorothioic dichlorides 5d-e in the presence of triethylamine at 45-65°C. Their IR, 1H, 13C, 31P NMR and mass spectral data are discussed. All these compounds are found to have significant antifungal and antibacterial activity.
- Venugopal,Reddy,Bavaji
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p. 822 - 827
(2007/10/03)
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