Structure of 56643-83-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 56643-83-5 |
Formula : | C14H14N4 |
M.W : | 238.29 |
SMILES Code : | C1(CN2C=CN=C2)=CC=C(CN3C=CN=C3)C=C1 |
MDL No. : | MFCD06598031 |
InChI Key : | NKUFFYFOBGGDTP-UHFFFAOYSA-N |
Pubchem ID : | 1257389 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 16 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 69.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.64 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.18 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.64 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.52 |
Solubility | 0.713 mg/ml ; 0.00299 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.64 |
Solubility | 5.48 mg/ml ; 0.023 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.27 |
Solubility | 0.0127 mg/ml ; 0.0000533 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.84 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.48 |
* 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 |
---|---|---|
In water; at 20℃; under 760.051 Torr; | General procedure: In a typical mechanochemical reaction, 0.09mmol of each reactant, i.e. 27mg of Co(NO3)2.6H2O (or 9mg of Co(OH)2 or 27mg of Zn(NO3)2·6H2O or 8mg of ZnO), 23mg of H2BrIP and 22mg of BIX, were taken in a mortar and gently kneaded with a pestle for 30?45min at ambient temperature. The desired crystalline product was obtained by the hydrothermal method when the metal salt:H2BrIP:BIX ratio was 1:1:2; however, the mechanochemical syntheses were executed with 1:1:1 reactants stoichiometry. The obtained material was allowed to stand overnight in an ambient atmosphere. In the case of liquid assisted grinding (LAG), 100muL solvent (water or methanol) was added to the dry reactants before grinding was commenced and kneading was performed for 15?30min. A color change was observed in all cases with an increase in grinding time and a violet colored homogeneous powder was obtained on completion of the reactions. Thus, Nitrate1Unknown node type: bNitrate1Neat, Nitrate1Unknown node type: bNitrate1MeOH, Hydroxide1Unknown node type: b2Unknown node type: bHydroxide1H2O, Nitrate1Unknown node type: b2Unknown node type: bNitrate1H2O, Nitrate2Unknown node type: b2Unknown node type: bNitrate2H2O and Oxide2Unknown node type: b2Unknown node type: bOxide2H2O were synthesized, where the subscripts ?Nitrate?, ?Hydroxide? or ?Oxide? indicate the anion of metal salts used and the superscripts ?Neat?, ?MeOH? or ?H2O? represent the solvent-free, methanol or water assisted kneading processes respectively. Thus, the subscripts and superscripts in the designated samples are used as identity to the metal precursor and grinding protocol respectively. The prepared samples were characterized by PXRD and FTIR analyses. Experimental elemental analysis did not show results consistent with calculated values due to varying minute amounts of the unreacted precursors. However, the samples prepared by LAG followed by washing with methanol or acetone showed expected elemental composition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In water; at 124.84℃; for 50h; | Co(NO3)2·6H2O (54mg, 0.18mmol), H2BrIP (45mg, 0.18mmol), BIX (90mg, 0.37mmol) and 9.5mL of distilled water in a 23mL Teflon-lined vessel were hydrothermally reacted at 398K for 50h and then cooled slowly to room temperature. A violet colored crystalline material along with X-ray quality crystals were obtained. The material was isolated in 57percent yield after washing with distilled water and methanol, and drying in air. Elemental analysis (percent): Calc.: C, 48.91; H, 3.17; N, 10.37; Obs.: C, 48.73; H, 3.32; N, 10.04. FTIR cm?1 (KBr): 3436 (br), 3097 (m), 2369 (w), 1617 (s), 1560 (m), 1428 (w), 1345 (s), 1244 (w), 1103 (m), 1027 (w), 951 (w), 889 (w), 766 (m), 733 (s), 660 (w), 444 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; under 760.051 Torr; | General procedure: In a typical mechanochemical reaction, 0.09mmol of each reactant, i.e. 27mg of Co(NO3)2.6H2O (or 9mg of Co(OH)2 or 27mg of Zn(NO3)2·6H2O or 8mg of ZnO), 23mg of H2BrIP and 22mg of BIX, were taken in a mortar and gently kneaded with a pestle for 30?45min at ambient temperature. The desired crystalline product was obtained by the hydrothermal method when the metal salt:H2BrIP:BIX ratio was 1:1:2; however, the mechanochemical syntheses were executed with 1:1:1 reactants stoichiometry. The obtained material was allowed to stand overnight in an ambient atmosphere. In the case of liquid assisted grinding (LAG), 100muL solvent (water or methanol) was added to the dry reactants before grinding was commenced and kneading was performed for 15?30min. A color change was observed in all cases with an increase in grinding time and a violet colored homogeneous powder was obtained on completion of the reactions. Thus, Nitrate1Unknown node type: bNitrate1Neat, Nitrate1Unknown node type: bNitrate1MeOH, Hydroxide1Unknown node type: b2Unknown node type: bHydroxide1H2O, Nitrate1Unknown node type: b2Unknown node type: bNitrate1H2O, Nitrate2Unknown node type: b2Unknown node type: bNitrate2H2O and Oxide2Unknown node type: b2Unknown node type: bOxide2H2O were synthesized, where the subscripts ?Nitrate?, ?Hydroxide? or ?Oxide? indicate the anion of metal salts used and the superscripts ?Neat?, ?MeOH? or ?H2O? represent the solvent-free, methanol or water assisted kneading processes respectively. Thus, the subscripts and superscripts in the designated samples are used as identity to the metal precursor and grinding protocol respectively. The prepared samples were characterized by PXRD and FTIR analyses. Experimental elemental analysis did not show results consistent with calculated values due to varying minute amounts of the unreacted precursors. However, the samples prepared by LAG followed by washing with methanol or acetone showed expected elemental composition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; under 760.051 Torr; | General procedure: In a typical mechanochemical reaction, 0.09mmol of each reactant, i.e. 27mg of Co(NO3)2.6H2O (or 9mg of Co(OH)2 or 27mg of Zn(NO3)2·6H2O or 8mg of ZnO), 23mg of H2BrIP and 22mg of BIX, were taken in a mortar and gently kneaded with a pestle for 30?45min at ambient temperature. The desired crystalline product was obtained by the hydrothermal method when the metal salt:H2BrIP:BIX ratio was 1:1:2; however, the mechanochemical syntheses were executed with 1:1:1 reactants stoichiometry. The obtained material was allowed to stand overnight in an ambient atmosphere. In the case of liquid assisted grinding (LAG), 100muL solvent (water or methanol) was added to the dry reactants before grinding was commenced and kneading was performed for 15?30min. A color change was observed in all cases with an increase in grinding time and a violet colored homogeneous powder was obtained on completion of the reactions. Thus, Nitrate1Unknown node type: bNitrate1Neat, Nitrate1Unknown node type: bNitrate1MeOH, Hydroxide1Unknown node type: b2Unknown node type: bHydroxide1H2O, Nitrate1Unknown node type: b2Unknown node type: bNitrate1H2O, Nitrate2Unknown node type: b2Unknown node type: bNitrate2H2O and Oxide2Unknown node type: b2Unknown node type: bOxide2H2O were synthesized, where the subscripts ?Nitrate?, ?Hydroxide? or ?Oxide? indicate the anion of metal salts used and the superscripts ?Neat?, ?MeOH? or ?H2O? represent the solvent-free, methanol or water assisted kneading processes respectively. Thus, the subscripts and superscripts in the designated samples are used as identity to the metal precursor and grinding protocol respectively. The prepared samples were characterized by PXRD and FTIR analyses. Experimental elemental analysis did not show results consistent with calculated values due to varying minute amounts of the unreacted precursors. However, the samples prepared by LAG followed by washing with methanol or acetone showed expected elemental composition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium hydroxide; at 160℃; for 72.0h;Autoclave; High pressure; | Modifying the literature procedure for 3 [32], a mixture of Zn(NO3)26H2O (149 mg, 0.5 mmol), BIX2H2O (137 mg, 0.5 mmol),H3BTC (105 mg, 0.5 mmol) and NaOH (60 mg, 1.5 mmol) in 5 mLof distilled water was sealed in a 10 mL Teflon-lined stainless steelvessel, which was heated at 160 C for 3 days. Then the reactionsystem was cooled to room temperature within 39 h. Colorlesscrystals of compound 3 were obtained, separated by filtration,washed with water and dried in air. Yield: 202 mg, 66percent. IR (KBr):~m=cm1 = 1616 (s), 1581 (s), 1564 (s), 1526 (s), 1455 (m), 1370(s), 1289 (m), 1094 (m), 1025 (m), 827 (m), 777 (m), 737 (m),710 (m), 656 (m). Anal. Calc. for C23H20N4O8Zn2 (611.19 g/mol): C45.20. H 3.30, N 9.17. Found: C 46.07, H 3.44, N 9.51percent.Compounds 4?8 were prepared following the synthetic procedurefor 3 by reacting one equivalent of the metal salt with oneequivalent of BIX2H2O (137 mg, 0.5 mmol), one equivalent of thedi- or tricarboxylic acid and two or three equivalents of NaOH fordeprotonation depending on the number of acid protons. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With sodium hydroxide; at 160℃; for 72.0h;Autoclave; High pressure; | General procedure: Modifying the literature procedure for 3 [32], a mixture of Zn(NO3)26H2O (149 mg, 0.5 mmol), BIX2H2O (137 mg, 0.5 mmol),H3BTC (105 mg, 0.5 mmol) and NaOH (60 mg, 1.5 mmol) in 5 mLof distilled water was sealed in a 10 mL Teflon-lined stainless steelvessel, which was heated at 160 C for 3 days. Then the reactionsystem was cooled to room temperature within 39 h.Compounds 4?8 were prepared following the synthetic procedurefor 3 by reacting one equivalent of the metal salt with oneequivalent of BIX2H2O (137 mg, 0.5 mmol), one equivalent of thedi- or tricarboxylic acid and two or three equivalents of NaOH fordeprotonation depending on the number of acid protons. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In 1,4-dioxane; water; at 100℃; for 48h;Sealed tube; | A mixture of H3TCPB (0.002 mmol, 0.9 mg), bimb (0.004 mmol,1.2 mg), MnCl2*4H2O (0.008 mmol, 1.6 mg) and 1 mL DMF/1,4-dioxane/H2O (v/v/v = 1/1/2) was transferred to hard glass tube, heated at 100 C for 48 h. After being cooled to room temperature with the falling rate of 2.5 C/h, the pale yellow lump crystals of 2 were obtained withthe yield of 35% (based on H3TCPB). Anal. (%) calcd. ForC74H58Mn3N6O20: C, 63.78; H, 5.66, N, 5.55. Found (%): C, 63.50;H, 5.42, N, 5.54. IR (KBr pellet, cm-1): 3429(w), 1683(s), 1589(w),1504(s), 1398(s), 1336(s), 1220(s), 1114(m), 1002(s), 860(w), 783(m)(Fig. S1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.34% | In N,N-dimethyl-formamide; at 70 - 120℃; for 94.5h; | For the complex 2, we mixed 0.30 mmol and 0.095 g H3L with 0.30 mmol and 0.072 g pbix and 0.60 mmol and 0.178 g Co(NO3)2•6H2O to produce a mixture, and stirred the acquired mixture for half an hour at 70C in DMF and H2O mixture (with the volume rate of 2:8, mL). The above mixture was then kept in the glass bottle (25 mL) and heated for 94 hours at 120C, and after that, we cooled this mixture to the ambient temperature with 10C/h rate. Thus, we can gain the pink crystals of the complex 2 (with 47.34% and 0.089 g yield and on the basis of H3L). Anal. calcd for the C30H29N5O8Co: N, 10.83; H, 4.52 and C, 55.73; %. Found: N, 10.12%; H, 3.98 and C, 55.44. IR (KBr, cm-1): 731(m), 785(m), 1097(m), 1275(s), 1352(s), 1416(m), 1522(m), 1578(vs), 1618(m), 1678(m), 2910(w), 3016(w), 3134(m), 3383(m), 3529 (vs). |
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