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CAS No. : | 64-77-7 | MDL No. : | |
Formula : | C12H18N2O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JLRGJRBPOGGCBT-UHFFFAOYSA-N |
M.W : | 270.35 | Pubchem ID : | 5505 |
Synonyms : |
D 860;HLS 831;Tolbutamide, Artosin, Diabetol, Orinase;U-2043;NSC 87833;NSC 23813
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 69.92 |
TPSA : | 83.65 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.29 cm/s |
Log Po/w (iLOGP) : | 1.54 |
Log Po/w (XLOGP3) : | 2.34 |
Log Po/w (WLOGP) : | 2.86 |
Log Po/w (MLOGP) : | 1.21 |
Log Po/w (SILICOS-IT) : | 1.08 |
Consensus Log Po/w : | 1.81 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.78 |
Solubility : | 0.454 mg/ml ; 0.00168 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.74 |
Solubility : | 0.0496 mg/ml ; 0.000184 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.36 |
Solubility : | 0.0117 mg/ml ; 0.0000433 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.42 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
21% | With SoLo-D241G unspecific peroxygenase; dihydrogen peroxide; ascorbic acid; In aq. phosphate buffer; acetonitrile; at 30℃; for 1h;pH 7.0;Enzymatic reaction;Catalytic behavior; | General procedure: Reaction mixtures (1mL) contained purified peroxygenases (PaDa-I, JaWa, SoLo and SoLo-D241G mutants, 0.1muM), substrate (1mM, dissolved in 10% acetonitrile), potassium phosphate buffer (100mM, pH 7.0), ascorbic acid (4mM) and a single dosage of H2O2 (1mM). All reactions were stirred at 30C for one hour until reaction stopped. |
With glucose-6-phosphate dehydrogenase; DL-dithiothreitol; human cytochrome P450 2C9; NADP; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; NADPH-P450 reductase; In aq. phosphate buffer; at 37℃; for 0.0333333h;pH 7.4;Enzymatic reaction; | General procedure: Assays were done as described previously (4) with minorchanges. Typical incubations included 0.2 M P450 4A11, 0.4M NADPH-P450 reductase, 0.4 M b5, 150 M L--dilauroylsn-glycero-3-phosphocholine (DLPC; Sigma-Aldrich), 100 mMpotassium phosphate buffer (pH 7.4), and the indicated concentrationof lauric acid ([1-14C]lauric acid, usually added as anaqueous 10 mM solution of sodium laurate) in a final volume of0.25 ml. b5 was included because it stimulates the catalyticactivity (4). Following temperature equilibration to 37 C for 5min, reactions were initiated by the addition of an NADPHregeneratingsystem consisting of 0.5 mM NADP, 10 mM glucose6-phosphate, and 1 IU ml1 yeast glucose 6-phosphate dehydrogenase (66). Reactions generally proceeded at 37 C for2 min and were terminated with 1.0 ml of ethyl acetate containing0.1% CH3CO2H (v/v), and, following mixing with a vortexdevice, the mixtures were centrifuged (103 g for 10 min). A0.8-ml aliquot of the ethyl acetate layer (upper phase) was transferredto a clean tube, and the solvent was removed under anN2stream.The dried extracts were dissolved in 200l of a 1:1 mixture ofH2O/CH3CN containing 0.1% CH3CO2H (v/v) and 10 Mbutylated hydroxytoluene, and aliquots were analyzed on areversed-phase (octadecylsilane, C18) HPLC column (5 m,2.1 100 mm (Waters, Milford, MA)) coupled with a radioactivitydetector (-RAM, IN/US Systems, Tampa, FL). Reactionproducts and substrate were eluted at a flow rate of 0.6 mlmin1 using an increasing linear gradient ofCH3CN(including0.1% (v/v) HCO2H) from 35 to 95% (v/v) over 30 min.Assays with P450s other than P450 4A11 were performed asdescribed previously, with the modification of either preincubationwith DTT (1 mM) for 10 min or not (the DTT remainedin the reactions): P450 2C8-paclitaxel as substrate (67), P4502C9-<strong>[64-77-7]tolbutamid</strong>e as substrate (68), P450 2D6-bufuralol assubstrate (69), P450 3A4-nifedipine as substrate (70), P45019A1-testosterone as substrate (71), P450 21A2-progesteroneas substrate (72), P450 2A6-coumarin as substrate (73), andP450s 1B1-, 1A1-, and 1A2-7-ethoxyresorufin as substrate(74). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
and the further antidiabetic compound is selected from the group consisting of ... glibenclamide, acetohexamide, chloropropamide, glibornuride, tolbutamide, tolazamide, glipizide, carbutamide, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | In water; N,N-dimethyl-formamide; | b. Hydroxyethyl n-butyl carbamate (6.84 g.) and p-toluenesulfonamide (4.10 g. as sodium salt) in DMF (175 ml.) were heated at 110 for 3 hours. The product was filtered, the solvent evaporated in vacuo, and the residue taken up in water (100 ml.). A small insoluble residue of unreacted sulfonamide (500 mg., 7.3%) remained. The pH of the solution was adjusted to 8 with 10% aqueous acetic acid and the resulting precipitate was filtered off. The filtrate was acidified with 10% aqueous acetic acid to yield crude 1-(p-toluenesulfonyl)-3-n-butyl-urea (1.8 g., 18%). One recrystallization gave a sample m.p. 126-128 (i-r identical with authentic sample). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With SoLo-D241G unspecific peroxygenase; dihydrogen peroxide; ascorbic acid; In aq. phosphate buffer; acetonitrile; at 30℃; for 1h;pH 7.0;Enzymatic reaction;Catalytic behavior; | General procedure: Reaction mixtures (1mL) contained purified peroxygenases (PaDa-I, JaWa, SoLo and SoLo-D241G mutants, 0.1muM), substrate (1mM, dissolved in 10% acetonitrile), potassium phosphate buffer (100mM, pH 7.0), ascorbic acid (4mM) and a single dosage of H2O2 (1mM). All reactions were stirred at 30C for one hour until reaction stopped. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethyl acetate; at 20℃; for 24h; | Take 21.6 mg of <strong>[64-77-7]tolbutamid</strong>e and 10.8 mgMetformin is placed in a 4 mL vial,Add 2 mL of ethyl acetate,Ultrasound,To dissolve and supersaturate,The reaction was crystallized at room temperature for 24 hours.Centrifuge the suspension and discard the supernatant.The centrifuged solid was dried in a blast oven at 40 C for 3 hours.The metformin-toluene sulfonate type can be obtained.Its XRPD results are shown in Figure 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: N-butylamine; phenyl chloroformate With tributyl-amine In chloroform at 0℃; for 0.00833333h; Flow reactor; Large scale; Stage #2: toluene-4-sulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform; acetonitrile at 80℃; for 8h; Flow reactor; Large scale; | Procedure 3: Multistep Continuous-Flow Preparation of Sulfonylureas 1a-c General procedure: A solution of amine 5 premixed with a TBA in CHCl3 and a solution of chloroformate 4 in CHCl3 were pumped into the first reactor, a 2 mL glass reactor held at 0 °C using two separate full 10 mL SGE glass syringes to afford carbamate 2 in situ (Figure S3). A solution of sulfonamide3 premixed with DBU in MeCN was pumped using a full 10 mL SGE glass syringe to subsequently react with carbamate 2 in the second reactor held at 80 °C to afford sulfonylurea 1. The reaction was monitored by following sulfonylurea 1 by HPLC. After optimisation, the reaction was scaled-up in a Chemtrix’s KiloFlow reactor system. HPLC pumps (Model: UI-22-410D) were then used to deliver reagents at this scale from 2.5 L stock solution bottles. After running the systemfor 8 h continuously, the carbamate sulfonylurea 1 solution was collected, concentrated under reduced pressure, and redissolved in DCM and washed with aq 0.1 N HCl (15 L). The organic phase was dried (MgSO4) and concentrated under vacuum to afford a white solid. The crude product was purified by crystallisation from a hexane/EtOAc mixture and oven dried at 60 °C and characterised by NMR spectroscopy. Gliclazide (1a). White solid; yield: 0.208 kg (87%); mp 165-169 °C. The NMR data were the same as given in procedure 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 3 h / 95 °C 2: sodium thiosulfate; water; methanol / 1 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; trichlorophosphate In toluene at 95℃; |