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CAS No. : | 676273-39-5 | MDL No. : | MFCD13177481 |
Formula : | C16H11IN2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IUOBIBLYALVHRN-UHFFFAOYSA-N |
M.W : | 422.24 | Pubchem ID : | 21955913 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.06 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 93.41 |
TPSA : | 71.24 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.06 cm/s |
Log Po/w (iLOGP) : | 2.8 |
Log Po/w (XLOGP3) : | 3.96 |
Log Po/w (WLOGP) : | 4.74 |
Log Po/w (MLOGP) : | 3.59 |
Log Po/w (SILICOS-IT) : | 3.28 |
Consensus Log Po/w : | 3.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.33 |
Solubility : | 0.002 mg/ml ; 0.00000473 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.16 |
Solubility : | 0.00294 mg/ml ; 0.00000697 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.23 |
Solubility : | 0.000251 mg/ml ; 0.000000594 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
95.5% | Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Stage #2: at 0 - 20℃; |
Preparation of compound 69b: 3-iodo-l-tosyl-l/7-indole-5-carbonitrileTo a solution of 3-iodo-l//-indole-5-carbonitrile (2 g, 7.40 mmol) in DMF (20 mL) was added 60percent NaH (538 mg, 22.38 mmol) portion wise at 0 °C and the reaction was stirred for 10 min RT. To the above mixture at 0 °C, p-TsCl (2.2 g, 11.19 mmol) solution in DMF (4 mL) was added and stirred for further 2 h at RT. The reaction was quenched with ice cold H20 (20 mL). The resulting suspension was filtered and the solid was washed with H20 (10 mL) and dried. The crude was purified with silica gel chromatography (eluent: 20percent EtOAc in petroleum ether) to afford 3-iodo-l-tosyl-l//-indole-5-carbonitrile (3.0 g, 95.5percent) as an off brown solid. .H NMR (400MHz, DMSO-d6): δ 8.30 (s, 1H), 8.13 (d, J=8.8Hz, 1H), 7.98 (d, J=8.4Hz, 2H), 7.87-7.81 (m, 2H), 7.43 (d, J=8.0Hz, 2H), 2.32 (s, 3H). |
91% | With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; Inert atmosphere | Example 2 Synthesis of 3-iodo-1-tosyl-1H-indole-5-carbonitrile (V) [0062] 3-iodo-1H-indole-5-carbonitrile (V), obtained as described in Example 1 (8.7 g, 32.5 mmol), NaOH (2.1 g, 52.5 mmol), triethylbenzylammonium chloride (0.7 g, 3.1 mmol) and tosyl chloride (6.7 g, 35.1 mmol) are suspended in CH2Cl2 (260 mL) under inert atmosphere, and the reaction mixture is maintained under stirring at ambient temperature overnight. The mixture is treated with water and the phases are separated. The organic phase is further washed with water and a saturated solution of NaCl, then dried on Na2SO4, filtered and concentrated at low pressure. Product (V) is thus obtained as a solid (12.5 g) with a yield of 91percent. [0063] 1H-NMR (400 MHz, CDCl3), δ: 8.02 (1H, d, J=8.4 Hz); 7.78-7.54 (3H, m); 7.69 (1H, s); 7.58 (1H, d, J=8.4 Hz); 7.26 (2H; d, J=8.0 Hz); 2.34 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium penicillin V; sodium thiosulfate In N,N-dimethyl-formamide | Example 1 Synthesis of 3-iodo-1H-indole-5-carbonitrile (V) 1H-indole-5-carbonitrile (5 g, 35.2 mmol), KOH (7.90 g, 141 mmol) and I2 (8.90 g, 35.2 mmol) are suspended in 25 mL of DMF under inert atmosphere. The reaction is maintained under stirring in the dark for 30 min. at 10°C, and then treated with an 0.1M solution of Na2S2O3 (150 mL). The resulting suspension is maintained under stirring for 30 min, then filtered, and the resulting solid is washed with water and dried at 50°C under vacuum to constant weight. Product (V) (9.0 g) is obtained as a white solid with a yield of 95percent. 1H-NMR (400 MHz, CDCl3), δ: 8.78 (1H, bs); 7.80 (1H, s); 7.46-7.40 (3H, m). |
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