Structure of 4-Thiobenzoic acid
CAS No.: 1074-36-8
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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. : | 1074-36-8 |
Formula : | C7H6O2S |
M.W : | 154.19 |
SMILES Code : | O=C(O)C1=CC=C(S)C=C1 |
MDL No. : | MFCD00016617 |
InChI Key : | LMJXSOYPAOSIPZ-UHFFFAOYSA-N |
Pubchem ID : | 95738 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H319-H332-H372-H400 |
Precautionary Statements: | P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
76.1 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.24 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.67 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.87 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.73 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.68 |
Solubility | 0.322 mg/ml ; 0.00209 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.63 |
Solubility | 0.0362 mg/ml ; 0.000235 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.87 |
Solubility | 2.1 mg/ml ; 0.0136 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 |
-5.54 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 |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 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) |
1.0 |
* 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 |
---|---|---|
INTERMEDIATE 30; This shows the preparation of 4-[5-(aminosulfonyl)-2-thienyl]thio}benzoic acid.To a solution of 5-bromothiophene-2-sulfonamide (242 mg) and 4-mercaptobenzoic acid (154 mg) in DMF (1 mL) was added aqueous 2 N sodium hydroxide solution (1 mL). The reaction mixture was heated in a CEM Discover microwave at 150C for 25 min. After this time it was allowed to cool, then it was diluted with water (20 mL) and acidified with 10 % v/v aqueous hydrochloric acid. The fine precipitate that formed was difficult to filter so the EPO <DP n="47"/>majority of the liquid was decanted from the solid, and the gelatinous residue concentrated to dryness in vacuo to give the title compound 4-[5-(aminosulfonyl)-2- thienyl]thio}benzoic acid (280mg).1H NMR (300 MHz, DMSO) δ 13.03 (s, 1H), 7.91 (d, 2H), 7.85 (s, 2H), 7.59 (d, 1H), 7.50 (d, 1H), 7.34 (d, 2H). | ||
With sodium hydroxide; In water; N,N-dimethyl-formamide; at 150℃; for 0.416667h;Microwave; | This shows the preparation of 4-[5-(aminosulfonyl)-2-thienyl]thio}benzoic acid.I0 To a solution of 5-bromothiophene-2-sulfonamide (242 mg) and 4-mercaptobenzoic acid (154 mg) in DMF (1 mL) was added aqueous 2 N sodium.hydroxide solution (1 mL). The reaction mixture was heated in a CEM Discover microwave at 1500C for 25 min. After this time it was allowed to cool, then it was diluted with water (20 mL) and acidified with 10% v/v aqueous hydrochloric acid. The fine precipitate that formed was difficult to filter is so the majority of the liquid was decanted from the solid, and the gelatinous residue concentrated to dryness in vacuo to give the title compound 4-[5-(aminosulfonyl)-2- thienyl]thio}benzoic acid (280 mg).1HNMR (300 MHz, DMSO) δ 13.03 (s, IH), 7.91 (d, 2H), 7.85 (s, 2H), 7.59 (d, IH), 7.50 (d, IH), 7.34 (d, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; In methanol; N,N-dimethyl-formamide; | A solution of 4-mercaptobenzoic acid (5.09 g, 33 mmol) in DMF (60 ml) was added to a slurry of 60percent NaOH (2.64 g, 66 mmol) in DMF (60 ml) under argon at 0° C. This mixture was stirred at 0° C. for 90 minutes prior to the dropwise addition of a solution of 1-(tert.-butyldimethylsilyloxy)-2-iodoethane (8.59 g, 30 mmol) in DMF (30 ml). The resultant reaction mixture was stirred for 3 hours at room temperature, then poured over a mixture of 0.5N HCl (70 ml) and ice (200 g) and diluted with water (500 ml). The precipitate that formed was collected by filtration to give a peach-colored solid (9.28 g, 99percent yield) which was used without further purification. The above product 4-[2[(t-butyldimethylsilyloxy)-ethyl]thio]benzoic acid (8.75 g, 28 mmol) was dissolved in CH3 OH (300 ml) containing conc. H2 SO4 (3 ml) and this solution was refluxed overnight. The solvent was removed by concentration, in vacuo, and the residue was partitioned between saturated NaHCO3 (300 ml) and ether (300 ml). The layers were separated and the aqueous phase extracted with EtOAc (200 ml). The combined organic extracts were dried over Na2 SO4 and concentrated, in vacuo, to give an orange gum which was purified by flash chromatography. Elution with hexane/EtOAc (2:1) yielded the product as a white solid (3.53 g, 59percent yield) which melted at 58° C. The following analyses indicate that that product was methyl 4-(2-hydroxyethyl)thio benzoate: NMR(CDCL3) delta=7.94(2H, d, J=8.5 Hz), 7.36(2H,, d J=8.5 Hz), 3.90(3H, s), 3.83(2H, q, J=6.1 Hz), 3.21 (2H, t, J=6.1 Hz), 1.96(1H, t, J=6.1 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; In methanol; N,N-dimethyl-formamide; | A solution of 4-mercaptobenzoic acid (5.09 g, 33 mmol) in DMF (60 ml) was added to a slurry of 60percent NaOH (2.64 g, 66 mmol) in DMF (60 ml) under argon at 0° C. This mixture was stirred at 0° C. for 90 minutes prior to the dropwise addition of a solution of 1-(tert.-butyldimethylsilyloxy)-2-iodoethane (8.59 g, 30 mmol) in DMF (30 ml). The resultant reaction mixture was stirred for 3 hours at room temperature, then poured over a mixture of 0.5N HCl (70 ml) and ice (200 g) and diluted with water (500 ml). The precipitate that formed was collected by filtration to give a peach-colored solid (9.28 g, 99percent yield) which was used without further purification. The above product 4-[2[(t-butyldimethylsilyloxy)ethyl]thio]benzoic acid (8.75 g, 28mmol) was dissolved in CH3 OH (300 ml) containing conc. H2 SO4 (3 ml) and this solution was refluxed overnight. The solvent was removed by concentration, in vacuo, and the residue was partitioned between saturated NaHCO3 (300 ml) and ether (300 ml). The layers were separated and the aqueous phase extracted with EtOAc (200 ml). The combined organic extracts were dried over Na2 SO4 and concentrated, in vacuo, to give an orange gum which was purified by flash chromatography. Elution with hexane/EtOAc (2:1) yielded the product as a white solid (3.53 g, 59percent yield) which melted at 58° C. The following analyses indicate that that product was methyl 4-(2-hydroxyethyl)thio benzoate: NMR(CDCL3) delta=7.94(2H, d, J=8.5 Hz), 7.36(2H, d, J=8.5 Hz), 3.90(3H, s), 3.83(2H, q, J=6.1 Hz), 3.21 (2H, t, J=6.1 Hz), 1.96(1H, t, J=6.1 Hz) |