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CAS No. : | 24573-15-7 | MDL No. : | MFCD00134383 |
Formula : | C10H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CEJJXIXKGPQQNG-UHFFFAOYSA-N |
M.W : | 188.18 | Pubchem ID : | 1712490 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.2 |
TPSA : | 50.92 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -13.18 cm/s |
Log Po/w (iLOGP) : | 0.43 |
Log Po/w (XLOGP3) : | -8.07 |
Log Po/w (WLOGP) : | 0.62 |
Log Po/w (MLOGP) : | 1.34 |
Log Po/w (SILICOS-IT) : | -0.15 |
Consensus Log Po/w : | -1.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 3.51 |
Solubility : | 608000.0 mg/ml ; 3230.0 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 7.75 |
Solubility : | 10700000000.0 mg/ml ; 56700000.0 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.38 |
Solubility : | 7.88 mg/ml ; 0.0419 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.82 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane; In acetonitrile; at 20℃; for 0.15h; | General procedure: To a solution of pyridine derivative 1 or tertiary amine 2(1 mmol) in acetonitrile (5 mL) was added 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane (1 g, 3 mmol). The resulting mixture was stirred at room temperature for an appropriate time (Table 2). After completion of the reaction as monitored by TLC, the reaction mixture was diluted with toluene (10 mL) and water (6 mL). The aqueous layer which contained the product was separated from theorganic layer and evaporated under reduced pressure toleave the product. The products were characterized on the basis of their melting points, elemental analysis and IR, 1HNMR and 13C NMR spectral analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethyl sulfate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With trichlorophosphate; for 3h;Reflux; Inert atmosphere; | Synthesis of 2,20-dichloro-4,40-bipyridine (B). Phosphorousoxychloride POCl3 (18.65 ml, 0.2 mol) was added to 4,40-bipyridine-N,N’-dioxide (A) (1.88 g, 10.0 mmol) and the solution was refluxedfor 3 hours. The reaction mixture was poured onto crushed ice andthen neutralized with saturated solution of K2CO3 to give a brightgreen precipitate. The crude product wasfiltered off, washed withacetone and dried under vacuum (1.78 g, 79% yield). The structureof the product was confirmed by 1H NMR, 13C NMR and ESI-MSanalysis. Without further purification it was used to obtain (1). |
Phosphorus oxychloride (100ml) was heated to 70C and pyridine (7. 1ML), PCIS (8. 1G) and [4,4'] BIPYRIDINYL 1, 1'dioxide (6.4g) were added portion wise over 30MIN. The mixture was then heated to reflux for 48 hours, cooled. The cooled mixture was poured drop wise onto ice with vigorous stirring, then still with ice cooling brought to pH 12-14 by adding LOM NAOH. Mixture was extracted with ethyl acetate, dried OVER NA2S04 and concentrated under reduced pressure. The residue was purified by passing the crude mixture down Kieselgel using 5: 95 THF: CH2CL2 as the eluent. Melting point: 239-240C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium hydroxide; In water; at 140℃; for 6h; | Synthesis of [Co(NNO)(4,4'-byp)NO3]·8H2O 2 Co(NO3)2·6H2O (0.1510 g, 0.5189 mmol), nicotinic acid N-oxide (0.1498 g, 1.076 mmol), 4,4'-byp (0.1605 g, 1.027 mmol) and KOH (0.0562 g, 1.003 mmol) were mixed in 60 ml of redistilled water. After stirring for 1 h, the mixture was placed in a 100 ml teflon-lined reactor and heated at 140 C for 5 h and then slowly cooled to room temperature. The solution was filtered off and the filtrate was allowed to evaporate slowly at room temperature. Yield ca. 68%. Anal. Calcd. for C16H28CoN4O14 (%): C 34.36, H 5.05, N 10.02. Found C 34.64, H 5.07, N 10.09. ESI-MS(+) m/z: 353 (70) [Co(NNO)(4,4'-byp)]+, 371 (15) [Co(NNO)(4,4'-byp)H2O]+. In the same conditions as in Section 2.3.1 , Co(NNO)2(H2O)4 complex was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In water; at 20℃; for 1h;pH 4.2; | Synthesis of [Co(PNO)2(4,4'-byp)]·6H2O 1 The preparation of the 1 was performed as follows: 0.298 g of Co(NO3)2·6H2O (1.024 mM) was dissolved in the solution obtained from the mixing of 0.276 g PNO (1.984 mM) and 0.1587 g 4,4'-byp (1.016 mM) in 30 ml of distilled water. pH of solution was adjusted to 4.2 by addition of NaOH. The solution has been intensively stirred magnetically for 1 h at room temperature. The white solid product was filtered. Red-brown crystals, suitable for X-ray analysis, were obtained from the filtrate by slow evaporation after standing one week at room temperature. Yield ca. 73%. Anal. Calcd. for C22H28CoN4O12 (%): C 44.08, H 4.71, N 9.83. Found C 44.15, H 4.29, N 9.71. ESI-MS(+) m/z: 532 (60) [NaCo(PNO)2(4,4'-byp)]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With potassium hydroxide; In water; at 140℃; for 6h; | Synthesis of [Co(INO)(4,4'-byp)NO3]·7H2O 3 The corresponding cobalt complex with isonicotinic acid N-oxide was prepared by similar method. Co(NO3)2·6H2O (0.1484 g, 0.5099 mmol), isonicotinic acid N-oxide (0.1500 g, 1.078 mmol), 4,4'-byp (0.1554 g, 0.995 mmol) and KOH (0.0585 g, 1.04 mmol) were used. After heating in the teflon-lined reactor, the resulting solution was filtered and the filtrate allowed to standing at room temperature. After two weeks red-brown precipitate was obtained. Yield ca. 56%. Anal. Calcd. for C16H26CoN4O13 (%): C 35.50, H 4.84, N 10.35. Found C 35.85, H 4.92, N 10.39. ESI-MS(+) m/z: 353 (60) [Co(INO)(4,4'-byp)]+. At the room temperature, Co(INO)2(H2O)6 complex was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 74% | With sodium hydroxide; at 120℃; for 120h;Autoclave; High pressure; | A mixture of Cd(NO3)2·4H2O (0.3mmol), 1,4-naphthalenedicarboxylate acid (1,4-H2NDC) (0.1mmol), 4,4?-bipyridine-N,N?dioxide (4,4?-dpdo) hydrate (0.1mmol), NaOH (0.2mmol) and distilled water (15mL) was stirred for 1h. The mixture was then transferred to a 25mL Teflon-lined steel autoclave and kept at 120C for 5days under autogenous pressure. After the mixture had been slowly cooled down to room temperature, block crystals of the products were obtained and washed with distilled water. Yield: ca. 74% for 1 (based on 1,4-H2NDC). The general chemical formula sum is C34H22Cd2N2O11. Anal. Calcd(%): C, 47.52; H, 2.58; N, 3.26. Found: C, 47.59; H, 2.63; N, 3.22. IR (cm-1, KBr pellet): 3487 (w), 3097(w), 1591(s), 1577(vs), 1511(s), 1479(s), 1408(vs), 1373(s), 1264(s), 1205(s), 1184(m), 1032(w), 979(w), 958(w), 854(m), 831(m), 794(m), 775(w), 745(m), 555(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With sodium hydroxide; at 120℃; for 120h;Autoclave; High pressure; | General procedure: A mixture of Cd(NO3)2·4H2O (0.3mmol), 1,4-naphthalenedicarboxylate acid (1,4-H2NDC) (0.1mmol), 4,4?-bipyridine-N,N?dioxide (4,4?-dpdo) hydrate (0.1mmol), NaOH (0.2mmol) and distilled water (15mL) was stirred for 1h. The mixture was then transferred to a 25mL Teflon-lined steel autoclave and kept at 120C for 5days under autogenous pressure. After the mixture had been slowly cooled down to room temperature, block crystals of the products were obtained and washed with distilled water. Yield: ca. 74% for 1 (based on 1,4-H2NDC). The general chemical formula sum is C34H22Cd2N2O11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The chemicals for the synthesis of the compounds were used aspurchased. For the preparation of the title compound, (1). Dioxouranium(VI)nitrate hexahydrate, UO2(NO3)2.6H2O 0.1505(g) was suspended into a 20 ml solution containing (1:1) methanol/watermixture. Similarly TPC 0.0850 (g) was suspended into a 20 ml ofacetonitrile. Both the solutions were stirred separately for 30 minat 40 C. On mixing both the solution resulted in a yellowish solutionwhich was continued to stir for another half an hour at 40 C.The 4-4’-bipyridine ligand 0.0442(g) was weighed and directlyadded to the beaker containing the above boiling suspensions,and the stirring was continued. A sudden colour change with theformation of turbid yellow solution was observed on adding the4-40Bipyridine ligand. 20 ml of acetonitrile was added into the reactionvessel and the turbidity disappeared (Scheme 1). The resultingclear yellowish solution was kept undisturbed for crystallisation.After 30 days clear yellow plate like crystals were formed whichfloated on the surface of the mother liquor. The crystals werefiltered and washed with small portions of methanol and was driedin air. IR selected bands (cm-1): 3101(m), 2924(m), 2852(m),2736(m),1653(s), 1512(s), 1490(s), 1438(s), 1384(s), 1323(s),1273(s), 1219(s), 1118(s), 1085(s), 1029(s), 1002(m),862(s),817(s), 771(s), 748(s), 717(s), 657(s), 609(s), 513(s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | 0.41 g (1.0 mmol) of di(p-fluorobenzyl)tin dichloride in 10 ml of methanol was added to a 25 ml hot stirring methanolic solution of the ligand L (0.30 g, 1.0 mmol). The solution mixture was refluxed for 3 h, then 0.103 g (0.5 mmol) of <strong>[24573-15-7]4,4'-bipyridine N,N'-dioxide</strong> hydrate in 5 ml of methanol was added slowly, the mixture was further refluxed for 2 h and filtered. The filtrate was allowed to stand at room temperature, whereupon yellow crystals formed.The product was filtered, washed with methanol and dried in air. Yield: 0.31 g, 53%; m.p.: 196-198 C. Anal. Calc. for C24H20Cl2N2F2O3Sn: C, 47.10; H, 3.29; N, 4.58. Found: C, 47.50; H, 3.58;N, 5.05%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol; at 80℃; for 4h; | An aqueous solution (5 mL) of disodium 5-sulfosalicylate (Na2HSsal) (0.66 mmol, 0.172 g) was added dropwise to an aqueous solution (5 mL) of MnCl2·4H2O (1 mmol, 0.198 g) with constant stirring at room temperature (25 C). To the resulting mixture, a methanolic solution (10 mL) of dpyo (1 mmol, 0.188 g) was added dropwise and the light yellow reaction mixture was refluxed for 4 h at 80 C and then filtered. The filtrate was kept in a CaCl2 desiccator. After a few days, red crystals suitable for X-ray analysis were obtained. Yield 68%. Anal. Calc. for C44H48Mn2N6O26S2 (1250.88): C, 42.21; H, 3.83; N, 6.71. Found: C, 42.20; H, 3.84; N, 6.69%. IR (cm-1): 3200-3550 (br, vs), 2985 (vw), 1632 (w), 1548 (vs), 1484 (s), 1419 (vs), 1354 (s), 1302 (vw), 1218 (vs), 1192 (vs), 1082 (vw), 1030 (w), 904 (w), 859 (s), 833 (s), 704 (vw), 665 (s), 558 (s), 529 (vw), 483 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | A mixture of an aqueous solution of trichloroacetic acid(0.493 g, 3 mmol) and bp4do (0.564 g, 3 mmol) was stirred to givea clear solution, which was filtered and the filtrate allowed to standat room temperature. On evaporation, yellow block-shaped singlecrystals were obtained after 2 weeks. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 168h; | The single crystals of 3 were obtained by adding HReO4(0.979 g, 3 mmol) to an aqueous solution of bp4do (0.564 g,3 mmol). After one week, dark yellow block-shaped single crystalswere obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hexafluorophosphoric acid; In water; for 168h; | The single crystals of 2 were obtained by adding HPF6 (0.73 g,3 mmol) to an aqueous solution of bp4do (0.564 g, 3 mmol). Afterone week, light yellow block-shaped single crystals were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | A mixture of H3[PW12O40]·12H2O (300mg, 0.1mmol), AgNO3·H2O (80mg, 0.4mmol), dpdo (90mg, 0.5mmol), and H2O (10mL) was stirred for 1h. The pH was adjusted to 1.5 with 1M HNO3, then the mixture was transferred to an 18mL Teflon-lined reactor and kept under autogenous pressure at 170C for 3days. The reactor was slowly cooled to room temperature over a period of 10C/h. Brown like block crystals of 1 were filtered, washed with water, and dried at room temperature. Yield: 40% based on Ag. C70H63Ag3N14O96P2W24 (7434): Calcd: C, 11.31; H, 0.85; N, 2.64; Ag, 4.35; P, 0.83; W, 59.35%; Found: C, 11.35; H, 0.92; N, 2.60; Ag, 4.28; P, 0.85; W, 59.18%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With hydrogenchloride; In water; acetonitrile; at 110℃;Autoclave; High pressure; Sealed tube; | A mixture of [SiW12O40]4- (53.67 mg,0.015 mmol) dissolved in acetonitrile (3 mL), a solution of CoCl2·6H2O (14.27 mg, 0.06 mmol)in water (3 mL) and bpdo (37.61 mg, 0.2 mmol) in water (2.5 mL) were added together withstirring. The pH value of the mixture was carefully adjusted with a dilute HCl solution (1 molL-1) and the mixture stirred overnight. The resulting suspension was sealed in a 25 mL Teflonlinedreactor and kept at 110 C for 3 days. After cooling the autoclave to room temperature,red single crystals of Co-SiW were separated, washed with water and air-dried (55% yieldbased on [SiW12O40]4-). Anal. Calcd. for C60H58Cl2Co3N12O57SiW12 (4318.97) (%): Co, 4.12; Cl,1.65; W, 51.08; Si, 0.65; C, 16.80; N, 3.90; H, 1.22. Found (%): Co, 4.09; Cl, 1.64; W, 51.07; Si, 0.65;C, 16.68; N, 3.89; H, 1.21. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With hydrogenchloride; In water; acetonitrile; at 110℃;Autoclave; High pressure; Sealed tube; | General procedure: A mixture of [SiW12O40]4- (53.67 mg,0.015 mmol) dissolved in acetonitrile (3 mL), a solution of CoCl2·6H2O (14.27 mg, 0.06 mmol)in water (3 mL) and bpdo (37.61 mg, 0.2 mmol) in water (2.5 mL) were added together withstirring. The pH value of the mixture was carefully adjusted with a dilute HCl solution (1 molL-1) and the mixture stirred overnight. The resulting suspension was sealed in a 25 mL Teflonlinedreactor and kept at 110 C for 3 days. After cooling the autoclave to room temperature,red single crystals of Co-SiW were separated, washed with water and air-dried (55% yieldbased on [SiW12O40]4-). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | at 20℃;pH 4.5;Heating; | Mixture of CuCl2 (0.1356 g, 0.08 mmol), Na8[p-sulfonatocalix[8]arene] (0.3131 g, 0.02 mmol), bpdo (0.3010 g, 0.16 mmol) with theratio of 4:1:8 (pH = 4.5) was dissolved in 30 mL hot water. Deep green crystals of the title compound 1 [Cu4(bpdo)6.12H2O.(p-sulfonatocalix[8]arene)].17H2O were obtained after volatilizing at room temperature for a few days (0.0917 g, yield: 31%, based on p-sulfonatocalix[8]arenes). Microanalysis (CHN) was not feasible due to the highly hydrated nature of the complexes. |