Structure of 42972-13-4
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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. : | 42972-13-4 |
Formula : | C9H6N2O4 |
M.W : | 206.16 |
SMILES Code : | O=C(C1=CC2=C(C(NNC2=O)=O)C=C1)O |
MDL No. : | MFCD06371360 |
InChI Key : | FXXJJBDOKNNGQF-UHFFFAOYSA-N |
Pubchem ID : | 309056 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 52.15 |
TPSA ? Topological Polar Surface Area: Calculated from |
103.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.36 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.09 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.56 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.32 |
Solubility | 9.9 mg/ml ; 0.048 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.34 |
Solubility | 9.4 mg/ml ; 0.0456 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.52 |
Solubility | 0.618 mg/ml ; 0.003 mol/l |
Class? Solubility class: Log S scale |
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 |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
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) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.81 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 |
0.56 |
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) |
1.75 |
* 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 |
---|---|---|
85% | With hydrazine; In acetic acid; at 120℃; for 2h; | Example K-I: 2-Isopropyl-7-methoxymethyl-4-(5-methyl-lH-pyrazol-3-ylamino')-2H-phthalazin- 1-onel,4-Dioxo-l,2,3,4-tetrahydro-phthalazine-6-carboxylic acidHydrazine hydrate (26g, 0.52mol) was added in one portion to a stirred mixture of 1,2,4-benzenetricarboxylic anhydride (10Og, 0.52mol), in acetic acid (1.0L) at room temperature. The mixture was heated to 120C for 2 hours and then allowed to cool to room temperature. The solid was filtered, washed with water (250ml) and dried in the vacuum oven at 500C for 20 hours to give the title compound (91g, 85% yield). |
85% | With acetic acid; hydrazine; at 20 - 120℃; for 2h;Product distribution / selectivity; | 1,4-Dioxo-1,2,3,4-tetrahydro-phthalazine-6-carboxylic acid: Hydrazine hydrate (26 g, 0.52 mol) was added in one portion to a stirred mixture of 1,2,4-benzenetricarboxylic anhydride (100 g, 0.52 mol), in HOAc (1.0 L) at RT. The mixture was heated to 120 C. for 2 hours and then allowed to cool to RT. The solid was filtered, washed with water (250 ml) and dried in the vacuum oven at 50 C. for 20 hours to give the title compound (91 g, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | l-Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acidl,4-Dioxo-l,2,3,4-tetrahydro-phthalazine-6-carboxylic acid (91.Og, 0.44mol) was suspended in dichloroethane (1.0L) and phosphorus pentabromide (761.Og,1.77mol) was added in three portions and the reaction heated to reflux for 24 hours. The reaction was cooled to room temperature and poured onto ice (2.50kg) EPO <DP n="177"/>and the resulting precipitate filtered and washed with water to give the crude product (13Og).This crude material was suspended in acetic acid (1.60L) and heated to 125C for 2 hours. The reaction was cooled to room temperature and poured onto ice (1.5kg) and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (85g, 73% yield) as a yellow solid. MS (ESI+) = (M+H)+ 310 & 312 | |
73% | Bromo-4-oxo-3,4-dihydro--phthalazine-6-carboxylic acid: 1,4-Dioxo-1,2,3,4-tetrahydrophthalazine-6-carboxylic acid (91.0 g, 0.44 mol) was suspended in DCE (1.0 L) and phosphorus pentabromide (761.0 g, 1.77 mol) was added in three portions and the reaction heated to reflux for 24 hours. The reaction was cooled to RT and poured onto ice (2.50 kg) and the resulting precipitate filtered and washed with water to give the crude product (130 g). |
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