- Synthesis and characterization of 6-substituted dibenzo [d,f][1,3,2] dioxa phosphepin 6-oxides
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Several 6-trichloromethyl dibenzo[d,f] [1,3,2] dioxaphosphepin 6-oxide (3a), 2-chloroethoxy dibenzo[d,f] [1,3,2] dioxaphosphepin 6-oxide (3b) and alkylcarbamato dibenzo [d,f] [1,3,2] dioxaphosphepin 6-oxides (6a-c) have been synthesized from reactions of equimolar quantities of 2,2'-dihydroxybiphenyl (1) with trichloromethylphosphonic dichloride (2a), O-2-chloroethyl phosphoryldichloride (2b) and dichlorophosphinyl carbamates (5a-c) at 45-50°C for (3a & 3b) and 40-45°C for (6a-c) in dry toluene in the presence of triethylamine. Elemental, IR and NMR (1H & 31P) data have been discussed and supported all structures.
- Kumar, K. Ananda,Reddy, C. Suresh,Rao, L. Nagaprasada,Raju, C. Naga
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- Conformation and Structure of Dichlorophosphoryl Isocyanate in the Gaseous and Solid Phases
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The conformational properties and the molecular structure of dichlorophosphoryl isocyanate, Cl2P(O)NCO, were studied by combining vibrational spectroscopy (IR and Raman), gas-phase electron diffraction (GED), X-ray crystallography (XRD), and quantum-chemical calculations. Computationally, two conformers of Cs symmetry with the P=O bond being in syn or anti configuration relative to the NCO group are predicted to be close in energy (ca. 2 kJ mol–1). Experimentally, both gas-phase and matrix-isolation IR spectra of Cl2P(O)NCO suggest the presence of a single conformer, which was determined to be the energetically more favorable syn-conformer. This was also found to exist in the solid state by low-temperature XRD. However, the molecule in the solid state is significantly distorted from ideal Cs symmetry with an O–P–N–C dihedral angle of 38.1(1)° due to intermolecular C···O contacts [2.881(4) ?]. In the gas phase, the GED analysis suggests that the molecule exists predominantly as syn-conformer but with dynamic behavior about the two minimum structures (syn and anti).
- Schwabedissen, Jan,Li, Dingqing,Reuter, Christian G.,Stammler, Hans-Georg,Mitzel, Norbert W.,Bernhardt, Eduard,Zeng, Xiaoqing
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- 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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p. 769 - 789
(2016/03/08)
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- N-phosphinyl ureas: Synthesis, characterization, X-ray structure, and in vitro evaluation of antitumor activity
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A new series of N-phosphinylureas 5b, 6a-7c was synthesized and characterized by 1H, 13C, 31P NMR, IR, and elemental analysis. The three-dimensional structure of 5b has been determined by X-ray crystallography. The crystal structure revealed the existence of four independent molecules. All structures form two chains with different arrangements and connect to each other via hydrogen bonds to produce two-dimensional polymeric chains. The cytotoxicity of cyclophosphamide (a standard antitumor compound) and its nine analogues with formula R 1C6H4 NHC(O)NHP(O)XCH2C(R 2)2 CH2Y(X = Y = NH, R2 = CH 3, R1 = H (5a), CH3 (5b), NO2 (5c), X = O, Y = NH, R2 = H, R1 = H (6a, CH3 (6b), NO2 (6c), and X = Y = O, R2 = CH3, R 1 = H (7a), CH3 (7b), NO2 (7c)) as well as phenyl urea were evaluated in vitro against three human tumor cell lines K562, MDA-MB-231, and HepG2. The results showed that most of the compounds have significant activity against the selected cell lines. Also, HepG2 cells were more sensitive to all the tested compounds than other cell lines.
- Gholivand, Khodayar,Dorosti, Nilufar,Ghaziany, Fatemeh,Mirshahi, Manouchehr,Sarikhani, Sina
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scheme or table
p. 74 - 83
(2012/04/10)
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- Synthesis, spectroscopic characterization, crystal structures, theoretical studies, and antibacterial evaluation of two novel N-phosphinyl ureas
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Two novel N-phosphinyl ureas containing different substituents were synthesized and characterized by 1H, 13C, and 31P NMR, IR, UV, mass spectroscopy, and elemental analysis. The crystal structures of these compounds were determined by X-ray crystallography. The structure of one compound exhibits the presence of two independent forms of the molecule with equal occupancy in the lattice and theoretical data reveal the same stabilization energies for these conformers. The title molecules have anti conformation with respect to the C=O and P=O bonds, whereas the other compound shows syn configuration. Quantum chemical calculations were applied to clarify this conformational behavior. Furthermore, the molecular geometry and vibrational frequencies of the new derivatives in the ground state were calculated by using the Hartree-Fock (HF) and density functional method (B3LYP) with 6-31+G* and 6-311+G* basis sets and compared with experimental values. The new derivatives were additionally tested in view of their antibacterial properties.
- Gholivand, Khodayar,Dorosti, Nilufar
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experimental part
p. 183 - 192
(2011/10/09)
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- Synthesis, characterisation and antimicrobial activity of novel 2-alkoxycarbonylamino-1,3,2-benzodiazaphosphole 2-oxides
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A series of some new class of 2-alkoxycarbonylamino-1,3,2- benzodiazaphosphole 2-oxides 4a-j were synthesised by reacting 3,4-diaminobenzophenone (3) with various dichlorophosphinyl carbamates (2) in drytoluene-tetrahydrofuran mixture (1:1) in the presence of triethylamine at 45-50°C. All the title compounds were evaluated for antimicrobial activity to determine their efficacy and were effective in suppressing the growth of bacteria and fungi. The chemical structures of the title products were characterised by IR, 1H, 13C and 31P NMR and mass spectral studies.
- Reddy, P. Vasu Govardhana,Bala Krishna,Reddy, M.V. Narayana,Annar,Reddy, C. Suresh
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body text
p. 65 - 67
(2009/10/15)
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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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p. 369 - 373
(2008/04/12)
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- Synthesis of carbamate derivatives of dibromodibenzo[d,g][1,3,6,2] dioxathiaphosphocin 6-oxides
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6-Alkylcarbamato-2,10-dibromodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6-oxides were prepared by cyclisation of 5,5′-dibromo-2,2′- dihydroxydiphenyl sulfide with dichlorophosphinyl carbamates/thiocarbamates, obtained by the addition of alcohols/thiols to dichloroisocyanatophosphine oxide, and characterised by IR, 1H, 13C, 31P NMR and mass spectral studies.
- Babu, Mesa Francis Stephen,Reddy, Cirandur Suresh
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p. 375 - 377
(2007/10/03)
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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 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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p. 535 - 537
(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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- N- AND O-BONDED CYANATO-DERIVATIVES OF THE HEXACHLOROPHOSPHATE - ION
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31P n.m.r. spectroscopy has led to the identification in solution of several ions in the series 6-n(NCO)n>- and 6-n(OCN)n>-, which were obtained by different preparative routes; iso
- Dillon, Keith B.,Platt, Andrew W. G.
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p. 299 - 304
(2007/10/02)
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- N-ALKYLIDENECARBAMOYL ISOCYANATES. REACTIONS WITH PHOSPHORUS CHLORIDES
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In the reactions of alkylidenecarbamoyl isocyanates with phosphorus trichloride, pentachloride, and oxychloride exchange of the isocyanate group by a chlorine atom occurs.In reaction with phosphorus pentachloride 1-methoxy-2,2,2-trifluoroethylidenecarbamoyl isocyanate gives the product from addition of the chlorine at the carbonyl group, i. e., N-(1-methoxy-2,2,2-trifluoroethylidene)-N'-chlorocarbonylcarbonimidoyl chloride.
- Gertsyuk, N. N.,Gorbatenko, V. I.,Samarai, L. I.
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p. 1233 - 1236
(2007/10/02)
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