Structure of 120-43-4
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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. : | 120-43-4 |
Formula : | C7H14N2O2 |
M.W : | 158.20 |
SMILES Code : | O=C(N1CCNCC1)OCC |
MDL No. : | MFCD00005964 |
InChI Key : | LNOQURRKNJKKBU-UHFFFAOYSA-N |
Pubchem ID : | 8431 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.86 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 48.85 |
TPSA ? Topological Polar Surface Area: Calculated from |
41.57 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.1 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.16 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.09 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.52 |
Solubility | 47.6 mg/ml ; 0.301 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.26 |
Solubility | 87.3 mg/ml ; 0.552 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.85 |
Solubility | 22.6 mg/ml ; 0.143 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 |
-7.38 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 |
1.0 |
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) |
2.0 |
* 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 |
---|---|---|
With potassium hydroxide; In ethanol; water; toluene; | The starting material can be manufactured, for example, as follows: 50 ml of ethanol, 50 g of potassium hydroxide and 8.8 ml of water are added to 39.8 g of 1-ethoxycarbonyl-4-[2-(3-chlorophenyl)-ethyl]-piperazine, obtainable by reacting 17.7 g of 1-ethoxycarbonylpiperazine and 24.6 g of 2-(3-chlorophenyl)-ethyl bromide while heating at 120-125 under nitrogen, and the whole is heated under reflux for 3 hours. The whole is then allowed to cool, is diluted with 300 ml of water and 300 ml of toluene and shaken thoroughly, and then the organic phase is separated off, washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. 1-[2-(3-chlorophenyl)-ethyl]piperazine is obtained and can be purified via the hydrochloride (m.p. 260) from which it can then be freed again by treatment with sodium hydroxide solution, separation with diethyl ether and evaporation of the latter. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h; | Example 133: 4-((S)-2-[5-(3,3-Dimethyl-2-oxo-butoxy)-1 -phenyl-1 H-pyrazole-3-carbonyl]- aminoJ-S-methoxycarbonylamino-propionyO-piperazine-i-carboxylic acid ethyl ester; (i) 4-((S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino-propionyl)- piperazine-1-carboxylic acid ethyl ester; To a solution of 5 g of (S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino- propionic acid, 3 g of triethylamine, 2.2 g of HOBT and 2.8 g of EDC in 50 ml of DCM, 2.3 g of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was then diluted with water and then extracted with 300 ml of DCM. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4. The solvents were removed under reduced pressure. The crude product was subjected to the next reaction step without further purification. Yield: 10.7 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethylmorpholine;; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 0℃; for 1h; | Example 92: 4-[(S)-4-Acetylamino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1- yl)-2-oxo-ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1 - carboxylic acid ethyl ester; i) 4-[(S)-4-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)- butyryl]-piperazine-1 -carboxylic acid ethyl ester; To a solution of 1.33 ml 1-ethoxycarbonylpiperazine, 1.27 ml N-ethylmorpholine and 4.0 g N-alpha-Fmoc-N-beta-Boc-L-diaminobutyric acid in 40 ml DMF were added 2.98 g TOTU at 0 0C. After 1 h the reaction mixture was diluted with 100 ml ethyl acetate and subsequently extracted with aqueous LiCI (4 percent), half-saturated aqueous NaHCO3 and water. The crude <n="118"/>product obtained after evaporation of the solvent was used in the subsequent reaction. Yield: 4.96 g colorless foam. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In methanol; at 20℃; for 12h; | General procedure: Lactone (1 mmol) in MeOH (5 mL) wasstirred, treated with a solution of piperazine (1 mmol) in MeOH (2 mL), and left at room temperature. The course of thereaction was monitored by TLC. If the product did not precipitate, the solvent was evaporated in vacuo after the reaction wascomplete. The residue was recrystallized from a suitable solvent (usually C6H6-hexane mixtures). Compounds 5a-e, 6a-d,and 7a,d,e were prepared by this method. |
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