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[ CAS No. 1198097-97-0 ] {[proInfo.proName]}

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Chemical Structure| 1198097-97-0
Chemical Structure| 1198097-97-0
Structure of 1198097-97-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1198097-97-0 ]

CAS No. :1198097-97-0 MDL No. :MFCD05885480
Formula : C10H8N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 220.25 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 1198097-97-0 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 63.57
TPSA : 100.98 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 0.83
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 1.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.891 mg/ml ; 0.00404 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.124 mg/ml ; 0.000564 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.36
Solubility : 0.953 mg/ml ; 0.00433 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.01

Safety of [ 1198097-97-0 ]

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 [ 1198097-97-0 ]

* 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 [ 1198097-97-0 ]
  • Downstream synthetic route of [ 1198097-97-0 ]

[ 1198097-97-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 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
  • 2
  • [ 3785-90-8 ]
  • [ 556-90-1 ]
  • [ 1198097-97-0 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 7, p. 961 - 978
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