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[ CAS No. 556-90-1 ] {[proInfo.proName]}

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Chemical Structure| 556-90-1
Chemical Structure| 556-90-1
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Product Details of [ 556-90-1 ]

CAS No. :556-90-1 MDL No. :MFCD00003186
Formula : C3H4N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 116.14 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 556-90-1 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.93
TPSA : 80.75 Ų

Pharmacokinetics

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) : -7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.56
Log Po/w (XLOGP3) : -0.25
Log Po/w (WLOGP) : -0.81
Log Po/w (MLOGP) : -1.35
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : -0.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.4
Solubility : 46.0 mg/ml ; 0.396 mol/l
Class : Very soluble
Log S (Ali) : -0.99
Solubility : 12.0 mg/ml ; 0.103 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.33
Solubility : 54.3 mg/ml ; 0.468 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.87

Safety of [ 556-90-1 ]

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 [ 556-90-1 ]

* 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 [ 556-90-1 ]
  • Downstream synthetic route of [ 556-90-1 ]

[ 556-90-1 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 107-14-2 ]
  • [ 17356-08-0 ]
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Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 2, p. 193 - 201
  • 2
  • [ 105-39-5 ]
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: for 0.166667 h; Reflux
Stage #2: for 3 h; Reflux
Thiourea (1.52g, 0.02mol) was added to 10mL 95percent ethanol. It was stirred at reflux for 10min, Slowly added dropwise ethyl chloroacetate (2.16mL, 0.02mol) then reflux for 3h. Cooling to room temperature, it was then filtered. Washed with a small amount of ethanol. Dried to give a white solid 2.51g, 92percent yield.
92% for 3 h; Reflux In a clean 50 mL single-necked flask, add 0.05 mol of thiourea,25.0 mL mass concentration of 95percent ethanol, Reflux stirring about 20min, so that thiourea all dissolved in 10min after the drop out of 0.05 mol ethyl chloroacetate, and then stirring reflux reaction 3h, A large amount of white fine crystals appeared in the resulting reaction solution, and the reaction solution was cooled to room temperature, followed by suction filtration and washing with a small amount of ethanol, finally drying, A solution of 2-imino-1,3-thiazolidin-4-one (7.40 g) as a white solid in 92percent yield, m.p. 222-224 °C.
86%
Stage #1: Reflux
Stage #2: With sodium acetate In water
A) Synthesis of 2-imino-4-thiazolidinone (IV):; 2Og (0.263mol) of thiourea (III) was added in 100ml round bottom flask, equipped with condenser, containing 50 ml ethanol. The mixture was gently refluxed. To this mixture 32.22g (0.263 mol) of ethylchloroacetate (II) was slowly added over a period of 30min. The mixture was refluxed and monitored on TLC. The reaction mixture was allowed to cool to room temperature. The hydrochloride salt of 2-imino- thiazolidin-4-one or pseudothiohydantoin was filtered from the solution. This salt was added to water and neutralized with solution of sodium acetate, which precipitates, 2-imino-4-thiazolidinone (TV) on cooling. The product was filtered and dried at 60°C. Yield : 86percent M. P. : 254-259°C
55% With sodium acetate In ethanol at 60℃; A solution of 239 (0.76 g, 10 mmoi), ethyl 2-chioroacetate (2.1 rnL, 20 mrnol). and sodium acetate in EtOFI (100 mL) is stirred at 60 °c overnight, After cooling to room temperature, the solid is collected to give 1)10 as a white solid (0.65 g, 55percent yield). (MS:[M+HJ 117.2)

Reference: [1] Patent: CN105884712, 2016, A, . Location in patent: Paragraph 0069; 0070; 0071
[2] Patent: CN104059060, 2017, B, . Location in patent: Paragraph 0058; 0059; 0060
[3] Patent: WO2010/82212, 2010, A2, . Location in patent: Page/Page column 28
[4] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0511
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6739 - 6745
  • 3
  • [ 17356-08-0 ]
  • [ 79-11-8 ]
  • [ 556-90-1 ]
Reference: [1] Organic Preparations and Procedures International, 2012, vol. 44, # 2, p. 184 - 186
[2] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 4, p. 897 - 903
[3] Tetrahedron, 2010, vol. 66, # 18, p. 3314 - 3317
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1953 - 1956
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 3, p. 835 - 844
[6] Letters in Drug Design and Discovery, 2011, vol. 8, # 7, p. 612 - 618
[7] Medicinal Chemistry Research, 2012, vol. 21, # 9, p. 2689 - 2701,13
[8] Bioorganic Chemistry, 2014, vol. 56, p. 27 - 33
  • 4
  • [ 94444-16-3 ]
  • [ 94444-15-2 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1097 - 1111
  • 5
  • [ 94417-85-3 ]
  • [ 94417-88-6 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1097 - 1111
  • 6
  • [ 81099-48-1 ]
  • [ 17356-08-0 ]
  • [ 556-90-1 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1982, vol. 16, # 9, p. 660 - 664[2] Khimiko-Farmatsevticheskii Zhurnal, 1982, vol. 16, # 9, p. 1060 - 1063
  • 7
  • [ 107-14-2 ]
  • [ 17356-08-0 ]
  • [ 921598-21-2 ]
  • [ 67355-26-4 ]
  • [ 556-90-1 ]
Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 2, p. 193 - 201
  • 8
  • [ 7404-50-4 ]
  • [ 556-90-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 1, p. 263 - 268
  • 9
  • [ 64-17-5 ]
  • [ 2315-37-9 ]
  • [ 17356-08-0 ]
  • [ 5326-84-1 ]
  • [ 556-90-1 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 5580,5582
  • 10
  • [ 2315-37-9 ]
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Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 5580,5582
  • 11
  • [ 17356-08-0 ]
  • [ 79-11-8 ]
  • [ 7404-50-4 ]
  • [ 5425-78-5 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 1, p. 263 - 268
  • 12
  • [ 64-17-5 ]
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Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1231
  • 13
  • [ 79-08-3 ]
  • [ 17356-08-0 ]
  • [ 73572-11-9 ]
  • [ 556-90-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 1, p. 263 - 268
  • 14
  • [ 2986-19-8 ]
  • [ 68-11-1 ]
  • [ 71-43-2 ]
  • [ 556-90-1 ]
Reference: [1] Annali di Chimica (Rome, Italy), 1953, vol. 43, p. 832,838
  • 15
  • [ 2986-19-8 ]
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  • [ 71-43-2 ]
  • [ 74-93-1 ]
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Reference: [1] Annali di Chimica (Rome, Italy), 1953, vol. 43, p. 832,838
  • 16
  • [ 123-08-0 ]
  • [ 556-90-1 ]
  • [ 1198097-97-0 ]
YieldReaction ConditionsOperation in experiment
61.8% for 3 h; Reflux General procedure: [0268] Synthesis of Compounds 120 to 122, which are (Z)-5-(substituted benzylidene)-2-iminothiazolidin-4-one analogs, was performed as follows. In detail, in an acetic acid (4 mL/1 g sodium acetate) solvent, a mixture including a substituted benzaldhehyde (300 mg), pseudothiohydantoin (1.1 eq.), and sodium acetate (3.0 eq.) was refluxed for 3 to 7 hours. Afier cooling, water was added thereto, and the produced precipitate was filtered, and in consideration of physical characteristics of the used starting materials, the resultant precipitate was washed with water and methylene chloride and/or ethyl acetate to obtain a solid target product. [0271] Orange solid; a reaction time of 3 hours; a yield of61.8percent; a melting point of >300° C.; ‘H NMR (500 MHz,DMSO-d5) ö 10.10 (s, 1H), 9.29 (brs, 1H), 9.04 (s, 1H), 7.49(s, 1H), 7.40 (d, 2H, J=9.0 Hz), 6.88 (d, 2H, J=8.5 Hz); ‘3CNMR (100 MHz, DMSO-d5) ö 181.4, 176.1, 159.6, 132.1,130.2, 126.0, 125.5, 116.8; ERMS (ES) mlz 219 (M-H)-.
61.8% for 3 h; Reflux General procedure: Synthesis of Compounds 120 to 122, which are (Z)-5-(substituted benzylidene)-2-iminothiazolidin-4-one analogs, was performed as follows. In detail, in an acetic acid (4 mL/1 g sodium acetate) solvent, a mixture including a substituted benzaldhehyde (300 mg), pseudothiohydantoin (1.1 eq.), and sodium acetate (3.0 eq.) was refluxed for 3 to 7 hours. After cooling, water was added thereto, and the produced precipitate was filtered, and in consideration of physical characteristics of the used starting materials, the resultant precipitate was washed with water and methylene chloride and/or ethyl acetate to obtain a solid target product.
61.8% for 3 h; Reflux General procedure: The desired compounds, (Z)-5-(substituted benzylidene)-2-iminothiazolidin-4-one analogues (1a– 1l) (Figure 1), were prepared by Knoevenagel condensation.With one exception, refluxing a solution of appropriate benzaldehydes and pseudothiohydantoinin acetic acid in the presence of NaOAc produced (Z)-5-benzylidene-2-iminothiazolidin-4-ones as a single stereoisomer in yields of 41.4–94.1percent. A Knoevenagel condensation between 2,4-dimethoxybenzaldehyde and pseudothiohydantoin under the same conditions gave amixture of (E)- and (Z)-5-(2,4-dimethoxybenzylidene)-2-iminothiazolidin-4-ones. These compounds could not be easily separated by conventional silica gel column chromatography. Milder reaction conditions capable of accomplishing the Knoevenagel condensation were needed to synthesize only (Z)-stereoisomer. Interestingly,heating a solution of 2,4-dimethoxy benzaldehyde and pseudothiohydantoin in ethanol:H2O (1:1) in the presence of 1.0 equiv. of piperidine as a base catalyst at 80 °C afforded the corresponding (Z)-stereoisomer(1l) as a sole product. A suspension of an appropriate benzaldehyde (300 mg, 1.53–2.46 mmol), pseudothiohydantoin(1.1 eq.), and sodium acetate (3.0 eq.) in acetic acid (1 mL/1 mmol of benzaldehyde) was refluxed for 3–7 h. The reaction mixture was cooled and water was added. The resulting precipitates were filtered, and washed with water and, if necessary, a small amount of methylene chloride or ethyl acetate, to produce (Z)-5-(substituted benzylidene)-2-iminothiazolidin-4-oneproducts (1a – 1k) in 41.4–94.1percent yields. The resulting precipitates were filtered, and washed with water,ethyl acetate and methylene chloride to give (Z)-5-(2,4-dimethoxybenzylidene)-2-iminothiazolidin-4-one (1l) all final products were confirmed by 1H and 13C NMR spectroscopy and mass spectroscopy. (Z)-5-(4-Hydroxybenzylidene)-2-iminothiazolidin-4-one (1a, MHY762) Orange colored solid; reaction time, 3 h; yield, 61.8percent; melting point, >300 °C; 1H-NMR (500 MHz, DMSO-d6)δ 10.10 (s, 1H, OH), 9.29 (br s, 1H, NH), 9.04 (s, 1H,NH), 7.49 (s, 1H, vinylic H), 7.40 (d, 2H, J = 9.0 Hz,2′-H, 6′-H), 6.88 (d, 2H, J = 8.5 Hz, 3′-H, 5′-H); 13CNMR(100 MHz, DMSO-d6) δ 181.4 (C-4), 176.1 (C-2),159.6 (C-4′), 132.1 (C-2′, C-6′), 130.2 (benzylic C), 126.0(C-5), 125.5 (C-1′), 116.8 (C-3′, C-5′); LRMS (ESI-) m/z 219 (M-H)-.
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 273 - 281
[2] Patent: US2014/23603, 2014, A1, . Location in patent: Paragraph 0268; 0271
[3] Patent: KR101677122, 2016, B1, . Location in patent: Paragraph 0411-0412; 0417
[4] Bioscience, Biotechnology and Biochemistry, 2018, vol. 82, # 5, p. 759 - 767
[5] Synthetic Communications, 2013, vol. 43, # 7, p. 961 - 978
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Reference: [1] Synthetic Communications, 2013, vol. 43, # 7, p. 961 - 978
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