Structure of 118996-38-6
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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. : | 118996-38-6 |
Formula : | C21H15NO6 |
M.W : | 377.35 |
SMILES Code : | O=C(O)C1=CC=C(N(C2=CC=C(C=C2)C(O)=O)C3=CC=C(C=C3)C(O)=O)C=C1 |
MDL No. : | MFCD22123674 |
InChI Key : | VEBUOOBGPZWCFE-UHFFFAOYSA-N |
Pubchem ID : | 53258191 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 28 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 102.0 |
TPSA ? Topological Polar Surface Area: Calculated from |
115.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.89 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.74 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.23 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.02 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.62 |
Solubility | 0.00915 mg/ml ; 0.0000242 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.85 |
Solubility | 0.000533 mg/ml ; 0.00000141 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.83 |
Solubility | 0.00558 mg/ml ; 0.0000148 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 |
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) |
Yes |
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 |
-5.95 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.06 |
* 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 |
---|---|---|
86.6% | With bromine; sodium hydroxide; In 1,4-dioxane; for 5h;Cooling with ice; | 3 ml of Br2 was added dropwise to a 30 ml solution of NaOH (7 g, 0.18 mol) in an ice bath.Stir for 20 min, then pour the solution into a constant pressure dropping funnel.The mixture was gradually added dropwise to a solution of 2.0 g of 4,4',4"-triacetyltriphenylamine in 1,4-dioxane (50 ml) for 5 hours at 45 C.The mixture was then subjected to an ice bath and saturated hydroxylamine HCl was added to reduce excess sodium bromide.Acidifying the solution with hydrochloric acid,The obtained solid product was filtered and dried under vacuum.Finally, the crude product is recrystallized from acetic acid.Obtaining the pure product 4,4',4"-tricarboxytriphenylamine H3TCA,It is a white solid. Yield: 86.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | Autoclave; High pressure; | H3TCA (0.019g,0.05mmol), H2NDC (0.0108g,0.05mmol) and EuCl3*6H2O (0.0732g, 0.2mmol)were dissolved in H2O (6mL),which were placed in a10 mL Teflon vessel within the autoclave. The mixture was heated at 125 C for 3 days and then cooled to room temperature at a rate of 5 C/h. Yellow block crystals of 1 were obtained (yield:15% based on EuCl3 * 6H2O). Elemental ana-lysis (%):Calcd for C33H22EuNO11: H,2.89;C,52.07;N,1.84.Found:H, 2.87;C,52.10;N,1.83.IR(KBr,cm1): 3413(s),2923(m),2530(m), 1684(s),1610(s),1404(s),1280(w),851(m),779(m),582(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | Autoclave; High pressure; | A mixture of H3TCA (0.019g, 0.05mmol), H2NDC (0.0108g, 0.05 mmol), TbCl3 6H2O (0.0747g, 0.2mmol), and H2O (6mL) was sealed in a 10mL Teflon-lined stainless steel autoclave, and heated at 125 C for 3 days under autogenous pressure. Then the system was cooled to room temperature at a rate of 5 C/h. Yellow block crystals of 2 were collected in 16% yield(based on TbCl3 * 6H2O). Elemental analysis (%): Calcd for C33H22TbNO11: H,2.87;C,51.60;N, 1.82. Found: H,2.86;C,51.57;N,1.85.IR(KBr,cm-1): 3399(s),2923 (w),2591(w),1930(w),1598(s),1404(s),1280(s),1183(m),851(m),779(m),582(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | In water; at 120.0℃; for 48h;Autoclave; | 2.1.4 Synthesis of [Mn3(L)2(py)4(H2O)]·H2O (4) A mixture of MnCl2·4H2O (10.2 mg, 0.05 mmol), py (0.5 mL, 0.05 mmol) and H3L (18.7 mg, 0.05 mmol) in 5 mL H2O at 120 C for 48 h afforded light yellow crystals of 4 in 38% yield based on MnCl2·4H2O. Elem anal. Calcd for C62H44Mn3N6O14: C, 59.01; H, 3.51; N, 6.66; Found: C, 59.12; H, 3.25; N, 6.75. IR (cm-1): 1594s, 1505m, 1499vs, 1397s, 1309m, 1267w, 1172m, 1113m, 1037w, 840s, 780vs, 699s, 671m, 625w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In ethanol; water; at 110.0℃; for 24h;Autoclave; | 2.1.1 Synthesis of [Mn3(L)(HCOO)3(DEF)3] (1) A mixture of MnCl2·4H2O (20.2 mg, 0.1 mmol) and H3L (38.3 mg, 0.1 mmol) in 5 mL DEF/EtOH/H2O (5:3:2, v: v:v) was sealed in a 20 mL Teflon-lined stainless vessel and subjected to 110 C for 24 h, and then cooled to room temperature. Yellow block-shaped crystals of 1 were obtained in 64% yield based on MnCl2·4H2O. Elem anal. Calcd for C39H48Mn3N4O15: C, 47.91; H, 4.95; N, 5.73; Found: C, 47.79; H, 4.74; N, 5.67. IR (cm-1): 1650w, 1617vs, 1598m, 1549vw, 1395s, 1309m, 1271w, 1169w, 1130w, 999w, 827w, 784m, 715w, 666w, 656w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | In water; at 120.0℃; for 48h;Autoclave; | A mixture of MnCl2·4H2O (20.2mg, 0.1mmol) and H3L (38.1mg, 0.1mmol) in 5mL DMF/H2O (7:3, v: v) was subjected to solvothermal condition at 120C for 48h, and then cooled to room temperature. Yellow block-shaped crystals of 3 were obtained (yield: 32%, based on MnCl2·4H2O). Elem anal. Calcd for C100H94Mn5N10O32: C, 54.04; H, 4.26; N, 6.30; Found: C, 54.11; H, 4.38; N, 6.17. IR (cm-1): 1650w, 1596m, 1534w, 1510w, 1459vw, 1407m, 1378m, 1311w, 1247m, 1173w, 1066s, 1035m, 901m, 850m, 783m, 737w, 672w, 631m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | In water; at 110.0℃; for 24h;Autoclave; | General procedure: 2.1.1 Synthesis of [Mn3(L)(HCOO)3(DEF)3] (1) A mixture of MnCl2·4H2O (20.2 mg, 0.1 mmol) and H3L (38.3 mg, 0.1 mmol) in 5 mL DEF/EtOH/H2O (5:3:2, v: v:v) was sealed in a 20 mL Teflon-lined stainless vessel and subjected to 110 C for 24 h, and then cooled to room temperature. Yellow block-shaped crystals of 1 were obtained in 64% yield based on MnCl2·4H2O. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.1% | With nitric acid; In water; acetonitrile; at 120.0℃; for 48h; | The raw material was weighed at a ratio of H3ntb: bpeb: Cu (NO3) 2: CH3CN: H2O: HNO3 of 33: 17: 50: 9110: 11090:Placed in a 50 mL glass beaker,Mixed for 1 h,Transferred to a 25 mL reactor,The reaction was carried out at 120 C for two days,Naturally cooled to room temperature,Observed pale green crystals,Ie target products,Filter it out from the mother liquor,Washed with water,After the natural dry.The obtained copper coordination polymer had an elemental analysis consistent with Example 1,Infrared,Fluorescence,X-ray powder diffraction characterization data.The present embodiment is repeated a plurality of times,According to the actual production of [Cu2 (Hntb) 2 (bpeb)] the quality of 27.5 ~ 28.5mg,The calculated yield was 94.6% ~ 98.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In water; N,N-dimethyl-formamide; at 140.0℃; for 72h;Sealed tube; | The mixture of Zn(CH3COO)2·2H2O (0.022 g, 0.100 mmol), H3TCA(0.037 g, 0.100 mmol) and Phen (0.018 g, 0.100 mmol) in 1 mL of dimethylformamide (DMF) and 5 mL H2O was sealed in a 15 mL vial,then transferred to the reaction of teflon reactor, heated to 140 C for 3 days, and then cooled to room temperature. The colorless block crystals obtained were washed with ethanol, and dried at room temperature (yield: 62%). Anal. calcd for C33H21N3O6Zn(%): C, 63.83; H, 3.41; N,6.77. Found: C, 63.78; H, 3.38; N, 6.76. IR (KBr, cm-1): 3396.72 (m),3072.80 (m), 2546.87 (m), 1676.28 (s), 1593.35 (s),1508.83 (s),1431.13 (s), 1413.87 (s), 1383.40 (s), 1314.86 (s),1288.25 (s),1173.35 (s), 1105.81 (m), 1016.61 (w), 943.53 (w),846.83 (s),782.78 (s), 725.78 (m), 711.25 (m), 682.12 (w),664.99 (w), 644.00(w), 549.24 (m), 514.10 (m), 445.79 (w). |
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