Home Cart Sign in  
Chemical Structure| 39736-29-3 Chemical Structure| 39736-29-3

Structure of 39736-29-3

Chemical Structure| 39736-29-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 39736-29-3 ]

CAS No. :39736-29-3
Formula : C7H10N2O2S2
M.W : 218.30
SMILES Code : O=C(C1=C(N)N=C(SC)S1)OCC
MDL No. :MFCD01830310
InChI Key :WAFDSQXKSGGKCD-UHFFFAOYSA-N
Pubchem ID :384908

Safety of [ 39736-29-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 39736-29-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 5
Fraction Csp3 0.43
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 54.33
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

118.75 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.27
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.55
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.63
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.46
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.8

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.82
Solubility 0.33 mg/ml ; 0.00151 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.69
Solubility 0.00445 mg/ml ; 0.0000204 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.92
Solubility 2.61 mg/ml ; 0.012 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.82 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.67

Application In Synthesis of [ 39736-29-3 ]

* 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 [ 39736-29-3 ]

[ 39736-29-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 623-51-8 ]
  • [ 10191-60-3 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
99% With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 5 h; The synthesis of ethyl 4-amino-2-(methylthio)thiazole-5-carboxylate
Ethyl 2-mercaptoacetate (50 g, 0.416 mol) was dissolved in 500 ml of dimethylformamide and added with dimethyl N-thienodithioimino carbonate (67 g, 0.416 mol) and diisopropylamine (112 ml, 0.624 mol).
After heating at 100° C. for 5 hours, the mixture was extracted with 500 ml of saturated ammonium chloride and 500 ml of ethylacetate, dried with sodium sulfate, filtered and concentrated under vacuum.
After washing the solid with n-hexane, the title compound (90 g, 99percent) was obtained.
1H-NMR (400 MHz, CDCl3); δ 5.84 (brs, 2H), 4.26 (q, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.32 (t, J=7.2 Hz, 3H); LC-MS 219 (MH+)
89% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; Ethyl 2-mercaptoacetate (5 g, 42 mmol, 1.0 eq) was dissolved in DMF (50 mL) and added with N-thienodi-thioimino carbonate (6.1 g, 42 mmol, 1.0 eq) and DIPEA (16.3 g, 126 mmol, 3.0 eq). After heating at 100 °C for 5 h, the mixture was diluted with saturated aqueous ammonium chloride (100 mL) and extracted with EtOAc (100 mLx2). The combined organic layer was washed with brine, dried, concentrated. The solid was washed with n-hexane and dried under vacuum to give the title compound (8 g, yield: 89percent) as a yellow solid. ESI-MS (M+H)+: 219.0.
References: [1] Patent: US2013/72482, 2013, A1, . Location in patent: Paragraph 0315-0317.
[2] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0468.
[3] Tetrahedron Letters, 1966, # 17, p. 1885 - 1889.
[4] Patent: WO2015/193506, 2015, A1, . Location in patent: Page/Page column 57-58.
  • 2
  • [ 10191-61-4 ]
  • [ 105-36-2 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: for 1 h; Reflux
Stage #2: With triethylamine In ethanol for 4 h; Reflux
The ethyl bromoacetate (1.96 g, 11.76 mmol) was added to a stirred solution of potassium methyl cyanimidodithiocarbonate 1 (2.0 g, 11.76 mmol) in EtOH (50 mL). The mixture was heated to reflux for 1 h. After cooling, Et3N (2.38 g, 23.52 mmol) was added and the mixture was heated to reflux for 4 h. The ethanol was evaporated and the residue was triturated with water (20 mL) followed by filtering. The solid was dried and then recrystallized from acetone to give compound 2 (2.4 g, 93percent). Light yellow solid; mp 101-103 °C; 1H NMR (400 MHz, CDCl3) δ (ppm): 5.80 (brs, 2H), 4.26 (q, 2H, J = 7.2 Hz), 2.63 (s, 3H), 1.32 (t, 3H, J = 7.2 Hz); HRMS (ESI) Calcd. for C7H11N2O2S2 [M+H]+: 219.0256; Found: 219.0248.
References: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5911 - 5920.
[2] Patent: WO2011/100838, 2011, A1, . Location in patent: Page/Page column 60; 61.
  • 3
  • [ 623-51-8 ]
  • [ 39736-29-3 ]
References: [1] Patent: US5326776, 1994, A, .
  • 4
  • [ 84911-18-2 ]
  • [ 10191-61-4 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
155 mg at 20℃; for 0.333333 h; Green chemistry General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11.
References: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 259 - 263.
  • 5
  • [ 55919-47-6 ]
  • [ 10191-61-4 ]
  • [ 39736-29-3 ]
YieldReaction ConditionsOperation in experiment
138 mg at 20℃; for 0.333333 h; Green chemistry General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11.
References: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 259 - 263.
  • 6
  • [ 105-39-5 ]
  • [ 39736-29-3 ]
References: [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 4, p. 1071 - 1076.
  • 7
  • [ 10191-61-4 ]
  • [ 105-39-5 ]
  • [ 39736-29-3 ]
References: [1] Tetrahedron, 1976, vol. 32, p. 623 - 627.
[2] Justus Liebigs Annalen der Chemie, 1972, vol. 764, p. 125 - 130.
  • 8
  • [ 10191-67-0 ]
  • [ 39736-29-3 ]
References: [1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 213 - 223.
  • 9
  • [ 10191-61-4 ]
  • [ 105-36-2 ]
  • [ 39736-29-3 ]
References: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 5, p. 1361 - 1366.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 39736-29-3 ]

Esters

Chemical Structure| 152300-59-9

A366896 [152300-59-9]

Ethyl 4-aminothiazole-5-carboxylate

Similarity: 0.90

Chemical Structure| 278183-10-1

A252490 [278183-10-1]

Methyl 4-amino-5-thiazolecarboxylate

Similarity: 0.87

Chemical Structure| 32955-22-9

A105981 [32955-22-9]

Ethyl 5-thiazolecarboxylate

Similarity: 0.80

Chemical Structure| 14527-44-7

A308629 [14527-44-7]

Methyl thiazole-5-carboxylate

Similarity: 0.77

Chemical Structure| 79836-78-5

A223135 [79836-78-5]

Ethyl 2-methylthiazole-5-carboxylate

Similarity: 0.73

Amines

Chemical Structure| 152300-59-9

A366896 [152300-59-9]

Ethyl 4-aminothiazole-5-carboxylate

Similarity: 0.90

Chemical Structure| 278183-10-1

A252490 [278183-10-1]

Methyl 4-amino-5-thiazolecarboxylate

Similarity: 0.87

Chemical Structure| 32955-21-8

A267020 [32955-21-8]

Ethyl 2-aminothiazole-5-carboxylate

Similarity: 0.71

Chemical Structure| 40283-46-3

A164763 [40283-46-3]

2-Aminothiazole-5-carboxylic acid

Similarity: 0.65

Chemical Structure| 7210-76-6

A175434 [7210-76-6]

Ethyl 2-amino-4-methylthiazole-5-carboxylate

Similarity: 0.61

Sulfides

Chemical Structure| 859522-19-3

A152741 [859522-19-3]

Ethyl 2-((2-aminothiazol-5-yl)thio)acetate

Similarity: 0.56

Related Parent Nucleus of
[ 39736-29-3 ]

Thiazoles

Chemical Structure| 152300-59-9

A366896 [152300-59-9]

Ethyl 4-aminothiazole-5-carboxylate

Similarity: 0.90

Chemical Structure| 278183-10-1

A252490 [278183-10-1]

Methyl 4-amino-5-thiazolecarboxylate

Similarity: 0.87

Chemical Structure| 32955-22-9

A105981 [32955-22-9]

Ethyl 5-thiazolecarboxylate

Similarity: 0.80

Chemical Structure| 14527-44-7

A308629 [14527-44-7]

Methyl thiazole-5-carboxylate

Similarity: 0.77

Chemical Structure| 14527-41-4

A212356 [14527-41-4]

5-Thiazolecarboxylic acid

Similarity: 0.73