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[ CAS No. 166737-85-5 ] {[proInfo.proName]}

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Chemical Structure| 166737-85-5
Chemical Structure| 166737-85-5
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Product Details of [ 166737-85-5 ]

CAS No. :166737-85-5 MDL No. :MFCD22126061
Formula : C22H22N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :OHWBGKONMFYEKL-FQEVSTJZSA-N
M.W : 362.49 Pubchem ID :44432703
Synonyms :

Calculated chemistry of [ 166737-85-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.14
Num. rotatable bonds : 7
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 107.89
TPSA : 94.41 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.63
Log Po/w (XLOGP3) : 3.69
Log Po/w (WLOGP) : 3.42
Log Po/w (MLOGP) : 3.52
Log Po/w (SILICOS-IT) : 3.89
Consensus Log Po/w : 3.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.46
Solubility : 0.0125 mg/ml ; 0.0000345 mol/l
Class : Moderately soluble
Log S (Ali) : -5.36
Solubility : 0.00157 mg/ml ; 0.00000434 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.23
Solubility : 0.0000215 mg/ml ; 0.0000000594 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.64

Safety of [ 166737-85-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 166737-85-5 ]

* 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.

  • Downstream synthetic route of [ 166737-85-5 ]

[ 166737-85-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 166737-85-5 ]
  • 3-{(4Z,10Z,15Z,19Z)-18-[2-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-ethyl]-3,8,13,17-tetramethyl-7,12-divinyl-22,24-dihydro-porphin-2-yl}-propionic acid [ No CAS ]
  • H-GGG-D(OtBu)PAALK(Boc)R(Pbf)AR(Pbf)N(Trt)T(tBu)E(OtBu)AAR(Pbf)R(Pbf)S(tBu)R(Pbf)AR(Pbf)K(Boc)LQ(Trt)R(Pbf)-NH-Novasyn TGR resin [ No CAS ]
  • protoporphyrin IX(-Cys-NH2)(-GGG-DPAALKRARNTEAARRSRARKLQR-NH2) [ No CAS ]
  • 2
  • [ 166737-85-5 ]
  • [ 286459-94-7 ]
  • (2R)-2-([14-(2-butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; In dichloromethane; for 13h; Example 13 (2R)-2-([14-(2-Butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide To a solution of 1.203g (3.685 mmol) of the primary amide product fromExample 12 and 1.39 ML (10 mmol) of triethylamine in 20 ML of methylene chloride was added in one portion 0.954g (3.9 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride.. After stirring for 13h, 50 ML of dichloromethane and 50 ML of water were added.. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and subjected to flash chromatography eluding with hexanes/ethyl acetate (1:1) to furnish 1.65g (79%) of the desired sulfonamide as a white solid.. Electrospray Mass Spec: 1139.6 (2M-H)
  • 3
  • [ 58885-35-1 ]
  • [ 166737-85-5 ]
YieldReaction ConditionsOperation in experiment
57% With ammonia; In methanol; at -78 - 20℃; for 14h; To 2.68g (7.37 mmol) of S-trityl-L-cysteine and 40 mL of methanol was added 7 mL (96 mmol) of thionyl chloride dropwise. After heating at reflux for 6h the solution was cooled to room temperature and then concentrated in vacuo. The resulting residue was taken up in 20 mL of methanol, treated with activated carbon, filtered and concentrated in vacuo yielding the methyl ester as an off-white foam. This material was dissolved in 6 mL of methanol in a sealable tube and cooled to -78. After 30 mL of liquid ammonia was added, the tube was sealed and the reaction was stirred at room temperature for 14h After recooling to -78 the reaction tube was unsealed and the solution was carefully reduced to dryness. The residue was chromatographed on silica gel eluting with methylene chloride/methanol (10:1) furnishing 1.52g (57%) of the primary amide as a white solid. Electrospray Mass Spec: 363.2 (M+H)+
  • 4
  • [ 166737-85-5 ]
  • (2R)-2-([14-(2-butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; water; 4-but-2-ynyloxybenzenesulfonyl chloride; EXAMPLE 13 (2R)-2-([4-(2-Butynyloxy)phenyl]sulfonyl}amino)-3-(tritylsulfanyl)propanamide To a solution of 1.203 g (3.685 mmol) of the primary amide product from Example 12 and 1.39 mL (10 mmol) of triethylamine in 20 mL of methylene chloride was added in one portion 0.954 g (3.9 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride. After stirring for 13 h, 50 mL of dichloromethane and 50 mL of water were added. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and subjected to flash chromatography eluding with hexanes/ethyl acetate (1:1) to furnish 1.65 g (79%) of the desired sulfonamide as a white solid. Electrospray Mass Spec: 1139.6 (2M-H)-
  • 5
  • [ 97802-29-4 ]
  • [ 166737-85-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In methanol; EXAMPLE 12 (2R)-2-Amino-3-(tritylsulfanyl)propanamide To 2.68 g (7.37 mmol) of S-trityl-L-cysteine and 40 mL of methanol was added 7 mL (96 mmol) of thionyl chloride dropwise. After heating at reflux for 6 h the solution was cooled to room temperature and then concentrated in vacuo. The resulting residue was taken up in 20 mL of methanol, treated with activated carbon, filtered and concentrated in vacuo yielding the methyl ester as an off-white foam. This material was dissolved in 6 mL of methanol in a sealable tube and cooled to -78.
  • 6
  • [ 166737-85-5 ]
  • N-[1-(1-benzothien-2-yl)-4-[tert-butyl(dimethyl)silyl]oxy}-1-(trifluoromethyl)but-2-yn-1-yl]-L-leucine [ No CAS ]
  • N-[(1R)-1-(1-benzothien-2-yl)-4-hydroxy-1-(trifluoromethyl)but-2-yn-1-yl]-L-leucyl-S-trityl-L-cysteinamide [ No CAS ]
  • N-[(1S)-1-(1-benzothien-2-yl)-4-hydroxy-1-(trifluoromethyl)but-2-yn-1-yl]-L-leucyl-S-trityl-L-cysteinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; triethylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h; To a solution of <strong>[166737-85-5]S-trityl-L-cysteinamide</strong> from Step 2, Example 2 (2.15 g, 6.15 mmol) in DMF (12.3 mL) was added 11ATU (2.28 g, 6 mol), HOBt (676 mg, 5 mmol) and N- [( 1 R)- 1 -( 1 -benzothien-2-yl)-4- { [tert-buty l(dimethyl)silyl]oxy }- 1 -(trifluoromethyl)but-2-yn- 1 -yl]- L-leucine (2.57 g, 5 mmol) from Step 3, Example 12. The mixture was cooled to 0C and Et3N (3.51 mL, 25 mmol) was added. The reaction was stirred at room temperature for 3 hours. Saturated aqueous NaHCO3, EtOAc:MTBE and water were added and the organic layer was separated. The aqueous layer was further extracted with 1 :1 EtOAc:MTBE. The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel ehiting with ethyl acetate and hexanes (3:2) to afford the title compound (1.14 g) enriched in the desired isomer. <n="69"/>1H NMR delta (PPm)(CD3COCD3): 6.85 and 6.6 (2H, NH2), 3.65 (1H, m), 3.2 (1H, m), 0.95 (6H, m); other resonances complex.
  • 7
  • [ 166737-85-5 ]
  • [ 1064622-37-2 ]
  • [ 1064622-45-2 ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxy-7-aza-benzotriazole; triethylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; To a solution of i<strong>[166737-85-5]S-trityl-L-cysteinamide</strong> from Step 2, Example 2 (235 mg, 0.65 mmol) in DMF (5 mL) was added HATU (209 mg, 0.55 mol), HOAt (68 mg, 0.5 mmol) and the N- [( 1 R)- 1 -(4-bromophenyl)-4-hy droxy- 1 -(trifluoromethyl)but-2-yn- 1 -y l]-4-fluoro-L-leucine from Step 4, Example 3 (220 mg, 0.5 mmol). The mixture was cooled to 0C and Et3N (0.35 mL, 2.5 mmol) was added. The reaction was stirred at room temperature overnight. Sat. aq. NaHCO3, EtOAc and water were added and the aqueous layer was extracted with EtOAc (3x). The combined organics were washed with brine (Ix), dried (MgSO4) and concentrated. The residue thus obtained was purified by column chromatography on silica gel eluting with 40% EtOAc/hexanes - > 60% EtOAc/hexanes - > 100% EtOAc to afford the title compound.1H NMR (500 MHz, d6-acetone) delta 7.8 (2H, d), 7.65-7.20 (17H, m), 6.6 and 6.8 (2H, 2 bs (NH2)), 4.5 (1H, m), 4.35 (2H, m), 4.25 (1H, m), 3.7 (1H, m), 3.3 (1H, m), 2.55-2.45 (2H, m), 2.25-2.15 (2H, m), 1.50-1.35 (6H, m).
  • 8
  • [ 202752-01-0 ]
  • [ 166737-85-5 ]
YieldReaction ConditionsOperation in experiment
92% With piperidine; In N,N-dimethyl-formamide; at 20℃; for 4h; A solution of the compound (R) - (9H-fluoren-9-yl) methyl (1-amino-1-oxo-3- (triphenylmethylthio) propan-2-yl) carbamate (4 g, 6.84 mmol )Was dissolved in N, N-dimethylformamide (20 ml)Piperidine (0.14 ml, 1.368 mmol) was added,Reaction at room temperature for 4 hours,TLC detection reaction is completed,The reaction mixture was washed with saturated brine,Extracted with dichloromethane,The organic phase was dried over sodium sulfate,concentrate,Column chromatography (methanol: dichloromethane = 1% -5%),The title product was obtained as a yellow oil (2.3 g, yield: 92%).
With pyrrolidine; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of 9H-fluoren-9-ylmethyl {(li?)-2-amino-2-oxo-1-[(tritylthio)methyl]-ethyl} carbamate (380 mg, 0.65 mmol) in DMF (3 mL) was added pyrrolidine (11 muL, 0.13 mmol). The reaction was stirred at room temperature overnight. By TLC and mass spectrometry, the reaction was deemed complete. This DMF solution of the title compound was used as such in the next reaction (Step 5, Example 3).
  • 9
  • [ 166737-85-5 ]
  • [ 225122-52-1 ]
  • [ 225122-70-3 ]
YieldReaction ConditionsOperation in experiment
A. N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-<strong>[166737-85-5]S-trityl-L-cysteinamide</strong> To a solution of 3-methyl-N-(2,2-diphenylacetyl-L-phenylalanine (see example 302, 1.0 g, 2.68 mmol), 1-hydroxybenzotriazole hydrate (0.41 g, 2.68 mmol) and N-methylmorpholine (0.74 ML, 6.69 mmol) in CH2Cl2 (80 ML) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (0.77 g, 4.02 mmol) in one portion.. After stirring 30 minutes at room temperature, <strong>[166737-85-5]S-trityl-L-cysteinamide</strong> (0.97 g, 2.68 mmol) is added to the solution in one portion, and the solution is stirred for 16 hours.. The solution is evaporated, and the residue partitioned between water (80 ML) and ethyl acetate (80 ML).. The aqueous layer is washed with EtOAc (2*80 ML), and the combined organic layers are then washed with 1 N HCl (100 ML), saturated aqueous NaHCO3 (1*50 ML), water (1*50 ML) and brine (1*50 ML), dried over MgSO4, and evaporated.. The residue is triturated with Et2O/hexane (1:1) to yield N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-<strong>[166737-85-5]S-trityl-L-cysteinamide</strong> as a white solid.
  • 10
  • [ 166737-85-5 ]
  • [ 27486-87-9 ]
  • [ 1129670-74-1 ]
  • 11
  • [ 166737-85-5 ]
  • C55H66N9O9PolS [ No CAS ]
  • [ 953424-20-9 ]
YieldReaction ConditionsOperation in experiment
The peptide, prepared as described above, was cleaved from the resin at RT by washing with a solution of 1% TFA in DCM by three repeated washings (15 min each). The resulting solution was neutralized by addition of DIPEA and concentrated to about 10% peptide content. Modification of the C-terminus was achieved by activation of the carboxy terminus with TBTU/HOBt and coupling with Cys(Trt)-NH2 solution in DCM. After removal of the solvent, the protected peptide was precipitated in water and dried. The protecting groups were removed using a 95% TFA, 2.5% TIS, 2.5% EDT solution for 2 hours at room temperature. The product was precipitated by the addition of 10 volumes of MTBE, filtered and dried in vacuum to obtain 32 g product.
  • 12
  • [ 166737-85-5 ]
  • [ 2799-07-7 ]
  • [ 81-30-1 ]
  • [ 1283599-82-5 ]
  • 13
  • [ 166737-85-5 ]
  • [ 81-30-1 ]
  • [ 5680-79-5 ]
  • [ 1283599-84-7 ]
  • 14
  • [ 166737-85-5 ]
  • [ 139-13-9 ]
  • C72H69N7O6S3 [ No CAS ]
  • 15
  • [ 166737-85-5 ]
  • [ 15442-91-8 ]
  • C32H30Br2N2OS [ No CAS ]
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