Structure of 13653-84-4
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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. : | 13653-84-4 |
Formula : | C20H14O4 |
M.W : | 318.32 |
SMILES Code : | O=C(C1=CC=C(C2=CC=C(C3=CC=C(C(O)=O)C=C3)C=C2)C=C1)O |
MDL No. : | MFCD00389774 |
InChI Key : | FZTIWOBQQYPTCJ-UHFFFAOYSA-N |
Pubchem ID : | 3369891 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
Num. heavy atoms | 24 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 91.23 |
TPSA ? Topological Polar Surface Area: Calculated from |
74.6 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.19 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.42 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.91 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.92 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.73 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.77 |
Solubility | 0.00541 mg/ml ; 0.000017 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.51 |
Solubility | 0.00099 mg/ml ; 0.00000311 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.16 |
Solubility | 0.000221 mg/ml ; 0.000000693 mol/l |
Class? Solubility class: Log S scale |
Poorly 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 |
-5.24 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) |
1.81 |
* 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 |
---|---|---|
31% | With triethylamine; at 20 - 105℃; for 48h; | Fe2(SO4)3.xH2O (0.19 g, 0.47 mmol) and 4,4'-terphenyldicarboxylic acid (H2TPDC) (0.15 g, 0.47 mmol) were placed in a 50 mL round bottom flask, to which 15 mL of N,N-dimethylformamide (DMF), 15 mL of pyridine, and 130 muL neat triethylamine (TEA) were added. The heterogeneous reaction mixture was capped and allowed to stir at room temperature for 24 h. A 6 mL aliquot of the stirring heterogeneous reaction solution and 4 mL of pyridine were added to a glass scintillation vial (20 mL capacity). The vial was capped and heated to 105 C. (5 C./min) for 24 h and cooled (0.5 C./min) to room temperature to give an orange/red homogeneous solution. After 4 days at room temperature, the orange product crystallized as plates of IRMOP-53 on the vial walls (31% yield based on H2TPDC). Crystals of IRMOP-53 were isolated, washed with 3×10 mL of pyridine, and 1×10 mL of cyclohexane. Anal. Calcd. for C252H274N28O77Fe12S12=[NH2(CH3)2]8[Fe12O4(SO4)12(TPDC)6(py)12].(py)7 (DMF) (C6H12)3: C, 50.60; H, 4.62; N, 6.56. Found: C, 50.59; H, 4.39; N, 6.48. FT-IR (KBr, 3500-400 cm-1): 3427 (s), 3074 (m), 2983 (m), 2807 (m), 2499 (w), 1607 (vs), 1593 (vs), 1555 (s), 1422 (vs), 1226 (s), 1146 (vs), 1120 (vs), 1038 (s), 1009 (s), 985 (s), 844 (w), 786 (s), 708 (m), 603 (m), 547 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
200 mg | To a stirred solution of 3-((6-aminohexyl)(tert-butoxycarbonyl)amino)-7-(tert-butoxycarbonyl amino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride (450 mg, 0.69 mmol) in 5 mL of DMF were added EDC.HC1 (i8i mg, 0.942 mmol), and HOBt (i27 mg, 0.942 mmol), and the mixture stirred for 5 mm. To this were added i,4-di(4-carboxyphenyl)benzene (100 mg, 0.314 mmol) and DIPEA (0.21 mL, i.25 mmol). The reaction mixture was stirred at RT for i2 h. After completion of reaction, the reaction mixture was diluted with ice-cold water and extracted with EtOAc. The organic layer was washed with brine (4x10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude product, which was purified by column chromatography (neutral alumina) to afford the desired product (200 mg). | |
200 mg | To a stirred solution of 3-((6-aminohexyl)(tert-butoxycarbonyl)amino)-7-(tert- butoxycarbonyl amino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride (450 mg, 0.69 mmol) in 5 mL of DMF were added EDC.HC1 (181 mg, 0.942 mmol), and HOBt (127 mg, 0.942 mmol), and the mixture stirred for 5 min. To this were added l,4-di(4-carboxyphenyl)benzene (100 mg, 0.314 mmol) and DIPEA (0.21 mL, 1.25 mmol). The reaction mixture was stirred at RT for 12 h. After completion of reaction, the reaction mixture was diluted with ice-cold water and extracted with EtOAc. The organic layer was washed with brine (4x10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude product, which was purified by column chromatography (neutral alumina) to afford the desired product (200 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With nitric acid; In N,N-dimethyl-formamide; at 130℃; for 72h;High pressure; Autoclave; | General procedure: A mixture of Co(NO3)2·6H2O (0.20mmol, 0.058g) and tib (0.20mmol, 0.056g) was dissolved in 8mL of DMF/H2O (1:1, v/v) with three drops of concentrated HNO3. The final mixture was placed in a Teflon-lined stainless steel vessel, heated to 130C for 3days, and then cooled (a descent rate of 5Ch-1) to room temperature. Purple block crystals of 1 were obtained. Yield of 53% (based on Co). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In N,N-dimethyl-formamide; at 120℃; for 72h;Sealed tube; | ZrCl4 (1.30 mg, 5.03 mumol), <strong>[13653-84-4]1,4-bis(4-carboxyphenyl)benzene</strong> (1.6 mg, 5.53 mumol) were dissolved in 0.8 mL of DMF in 1 dram vial, and 15.4 muL of trifluoroacetic acid was then added. The vial was capped and then heated at 12000 for 3 days to afford a white solid as the MOF product (2.0 mg, 95% yield). A transmission electron micrograph image of the as synthesized UiO-68-MOF is shown in FIG. 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In N,N-dimethyl-formamide; at 120℃; for 72h;Sonication; | To a 20 mL vial was added ZrCl4 (4.2 mg, 18 mumol), H2TPDC (5.7 mg, 18 mmol), acetic acid (0.75 mL), and DMF (10 mL). The mixture was sonicated for 5 min until all solids were dispersed and then kept in a 120 C. oven for 3 d. 3.1 mg of Zr12-TPDC (48% yield) was obtained as light gray powder. Characterization of Zr12-TPDC: FIG. 22 shows a transmission electron microscopy micrograph of the as-synthesized Zmu2-TPDC, showing a size distribution of about 50 nm. FIG. 23 shows the similarly between the PXRD patterns of Zr12-TPDC (top) with the simulated PXRD pattern (middle). The PXRD pattern of the Zr12-TPDC MOF is different from the UiO-68 MOF, which has a Zr6 SBU and the same TPDC linker. See FIG. 23, bottom. FIG. 24A shows a ball and stick model of the Zr12-TPDC MOF viewed along the [002] plane, while FIG. 24B shows a ball and stick model of Zr12-TPDC viewed along the [110] plane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | 1,4-bis(4-carboxyphenyl)benzene (420 mg, 1.21 mmol) was suspended in THF (65 mL). A solution of KOH (6.17 g, 110 mmol) dissolved in MeOH (20 mL) was then added, and the reaction mixture was stirred at 60 C. for 24 h. The suspension was cooled to room temperature and the resulting precipitate was collected by centrifugation. The solution was washed with dry THF (20 mL) and recollected by centrifugation. The solid was suspended in THF (20 mL) and trifluoroacetic acid (3 mL) was slowly added and stirred for 1.5 h at room temperature. H2O (15 mL) was then added, and the white solid was isolated by centrifugation, and subsequently washed with THF and Et2O, and dried in vacuo to obtain 1,4-bis(4-carboxyphenyl)benzene (331.9 mg, 1.04 mmol, 86% yield) as a pale-white solid. 1H NMR (500 MHz, DMSO-d6) delta 13.00 (br s, 2H), 8.05 (d, 4H, 3JHH=8.3 Hz), 7.89 (s, 4H), 7.88 (d, 4H, 3JHH=8.3 Hz). |
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