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[ CAS No. 18598-63-5 ] {[proInfo.proName]}

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Chemical Structure| 18598-63-5
Chemical Structure| 18598-63-5
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Product Details of [ 18598-63-5 ]

CAS No. :18598-63-5 MDL No. :
Formula : C4H10ClNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :WHOHXJZQBJXAKL-DFWYDOINSA-N
M.W : 171.65 Pubchem ID :2733208
Synonyms :
Mecysteine (hydrochloride);NSC 161611;Mecysteine HCl;Chistait;Mecysteine hydrochloride

Calculated chemistry of [ 18598-63-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.12
TPSA : 91.12 Ų

Pharmacokinetics

GI absorption : Low
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) : -7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.33
Log Po/w (WLOGP) : -3.47
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : -0.28
Consensus Log Po/w : -0.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.91
Solubility : 20.9 mg/ml ; 0.122 mol/l
Class : Very soluble
Log S (Ali) : -1.81
Solubility : 2.68 mg/ml ; 0.0156 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.13
Solubility : 127.0 mg/ml ; 0.741 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 18598-63-5 ]

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:

Application In Synthesis of [ 18598-63-5 ]

* 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.

  • Upstream synthesis route of [ 18598-63-5 ]
  • Downstream synthetic route of [ 18598-63-5 ]

[ 18598-63-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 18598-63-5 ]
  • [ 133145-19-4 ]
  • [ 23094-69-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 11, p. 2937 - 2944
  • 2
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  • [ 16858-01-8 ]
Reference: [1] Inorganic Chemistry, 2012, vol. 51, # 17, p. 9350 - 9356,7
  • 3
  • [ 4538-51-6 ]
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  • [ 93827-06-6 ]
  • [ 93921-43-8 ]
  • [ 76275-87-1 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 38, p. 4295 - 4298
[2] Tetrahedron Letters, 1984, vol. 25, # 38, p. 4295 - 4298
  • 4
  • [ 631-57-2 ]
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  • [ 76275-87-1 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 38, p. 4295 - 4298
  • 5
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  • [ 106-95-6 ]
  • [ 21593-77-1 ]
Reference: [1] Bioscience, Biotechnology and Biochemistry, 2018, vol. 82, # 4, p. 724 - 731
  • 6
  • [ 67-56-1 ]
  • [ 1447695-69-3 ]
  • [ 39994-75-7 ]
  • [ 6306-52-1 ]
  • [ 60667-85-8 ]
  • [ 18598-74-8 ]
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  • [ 2133-40-6 ]
Reference: [1] Journal of Natural Products, 2013, vol. 76, # 7, p. 1388 - 1391
  • 7
  • [ 67-56-1 ]
  • [ 1447695-69-3 ]
  • [ 39994-75-7 ]
  • [ 6306-52-1 ]
  • [ 60667-85-8 ]
  • [ 18598-74-8 ]
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  • [ 2133-40-6 ]
Reference: [1] Journal of Natural Products, 2013, vol. 76, # 7, p. 1388 - 1391
  • 8
  • [ 67-56-1 ]
  • [ 52-89-1 ]
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YieldReaction ConditionsOperation in experiment
85.9%
Stage #1: at 20℃; for 1 h; Cooling with ice; Inert atmosphere
Stage #2: at 20℃; for 4 h; Reflux
Under ice-bath condition, 3 ml SOCl2 was added dropwise to 35 ml methanol in the presence of nitrogen atmosphere. Afterward, the solution was stirred at room temperature for 1 h, then 1 g Cys·HCl·H2O was added in batches to the solution. And the mixture solution reacted at room temperature for 3 h, and then refluxed for 1 h. Removing the volatile component and solvent, the residue was recrystallized with CH3OH-CH2Cl2, and 0.84 g white solid was obtained with 85.9percent yield. IR (KBr, cm-1): 3040.4 (s, NH2), 1709.7 (s, C=O), 2580 (w, SH).
1H NMR (D2O, TMS, ppm); δ 4.453 (t, 1H, CH, J = 5.2 Hz), 3.871 (s, 3H, CH3), 3.164 (t, 2H, CH2, J = 6.4 Hz). Elemental Anal. Calcd for C4H10NO2SCl: C, 27.99; H, 5.87; N, 8.16percent. Found: C, 28.11; H, 6.01; N, 8.08percent.
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 199 - 215
[2] Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4270 - 4277
[3] Tetrahedron Asymmetry, 2000, vol. 11, # 21, p. 4255 - 4261
[4] Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5052 - 5053
[5] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 176 - 187,12
  • 9
  • [ 67-56-1 ]
  • [ 52-90-4 ]
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YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In methanol for 3 h; Reflux; Inert atmosphere General procedure: These compounds 11a-f were prepared using the generalmethod described by Gududuru et al. [35].Thionyl chloride (8.3 mL, 110 mmol) was added dropwise underan atmosphere of argon to a solution of L-cysteine (8) (9.00 g,74 mmol) in 150mL MeOH. The reaction mixture was refluxed for3 h then evaporated in vacuo, then co-evaporated with toluene(2 5 mL) to afford the hydrochloride salt of the methyl ester of Lcysteine(9) as white solid. One-sixth of this material (9)(12.4 mmol) was dissolved in water/ethanol (1:1) (15 mL). Sodiumhydrogen carbonate (1.14 g, 13.6 mmol) was added and, after10 min, the aromatic aldehyde (10a-f) (12.38 mmol) was added andthe reaction mixture was stirred for 14 h. The ethanol was evaporatedin vacuo and the aqueous residue was extracted with DCM(50 mL). The organic layer was washed with water (25 mL), driedover Na2SO4, filtered and evaporated in vacuo to afford the crudeproducts 11a-f.
96% at 0℃; for 2 h; Reflux General procedure: Acetyl chloride (1.6 mL, 22 mmol) was added to MeOH (100 mL), and the solution was cooled to 0°C. The solution was stirred for 5 min. Amino acid (L-serine, D-serine, L-cysteine, D-cysteine, L-2,3-diaminopropionic acid, and D-2,3-diaminopropionic acid) (20 mmol) was then added to the acetyl chloride solution in methanol (MeOH), and the solution was heated to reflux for 2 h, then cooled to room temperature.The reaction was evaporated under reduced pressure and gavea colorless solid. The solid was washed with CH2Cl2 (20 mL)to give amino acid methyl ester hydrochloride (2d–f, 2d–f)as a white solid. The yields of 2d, d, e, e, f and f were 95percent,96percent, 94percent, 96percent, 95percent, 95percent, respectively.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 462 - 479
[2] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 1, p. 33 - 37
[3] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 1, p. 54 - 62
[4] Canadian Journal of Chemistry, 1990, vol. 68, # 8, p. 1408 - 1419
[5] Tetrahedron Letters, 1989, vol. 30, # 9, p. 1041 - 1044
[6] Journal of the American Chemical Society, 1992, vol. 114, # 12, p. 4500 - 4514
[7] Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 9642 - 9643
[8] Magnetic Resonance in Chemistry, 2008, vol. 46, # 10, p. 986 - 989
[9] Journal of the American Chemical Society, 2009, vol. 131, # 45, p. 16346 - 16347
[10] Journal of the American Chemical Society, 2010, vol. 132, # 47, p. 16805 - 16811
[11] Patent: US2012/178913, 2012, A1, . Location in patent: Page/Page column 5
[12] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1170 - 1174
[13] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1237 - 1241
[14] Journal of Natural Products, 2013, vol. 76, # 7, p. 1388 - 1391
[15] Patent: CN103601742, 2016, B, . Location in patent: Paragraph 0102-0104
[16] Patent: CN105130871, 2018, B, . Location in patent: Paragraph 0038; 0042
  • 10
  • [ 52-90-4 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 6, p. 1554 - 1560
[2] Patent: US4745201, 1988, A,
  • 11
  • [ 67-56-1 ]
  • [ 1447695-69-3 ]
  • [ 39994-75-7 ]
  • [ 6306-52-1 ]
  • [ 60667-85-8 ]
  • [ 18598-74-8 ]
  • [ 18598-63-5 ]
  • [ 2133-40-6 ]
Reference: [1] Journal of Natural Products, 2013, vol. 76, # 7, p. 1388 - 1391
  • 12
  • [ 18598-63-5 ]
  • [ 220168-39-8 ]
  • [ 3532-25-0 ]
  • [ 32854-09-4 ]
  • [ 65-85-0 ]
Reference: [1] Australian Journal of Chemistry, 2011, vol. 64, # 4, p. 443 - 453
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