21344-90-1|4-(2-Chlorophenyl)thiazol-2-amine| Ambeed

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Quality Control of [ 21344-90-1 ] Purity: 98% SDS Specification

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Product Details of [ 21344-90-1 ]

CAS No. :	21344-90-1
Formula :	C₉H₇ClN₂S
M.W :	210.68
SMILES Code :	NC1=NC(C2=CC=CC=C2Cl)=CS1
MDL No. :	MFCD01315352
InChI Key :	GWXQQHVBVMLZLU-UHFFFAOYSA-N
Pubchem ID :	224764

Safety of [ 21344-90-1 ]

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

Computational Chemistry of [ 21344-90-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	56.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.87
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.05
Log P_o/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.	1.9
Log P_o/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	3.58
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.66

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.53
Solubility	0.0617 mg/ml ; 0.000293 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.	-3.97
Solubility	0.0225 mg/ml ; 0.000107 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.08
Solubility	0.0177 mg/ml ; 0.0000841 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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.	-5.53 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)	2.28

Application In Synthesis of [ 21344-90-1 ]

* 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.

Downstream synthetic route of [ 21344-90-1 ]

[ 21344-90-1 ] Synthesis Path-Downstream 1~35

1
[ 4755-77-5 ]
[ 21344-90-1 ]
N-[4-(2-Chloro-phenyl)-thiazol-2-yl]-oxalamic acid ethyl ester [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1391 - 1393.

2
[ 2142-68-9 ]
[ 17356-08-0 ]
[ 21344-90-1 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 75%	With iodine; for 0.0833333h;Microwave irradiation; Green chemistry;	CPAT was synthesized (Reaction 1) [22] by reacting 2'-chloroacetophenone (0.05 mol), iodine (0.1 mol) and thiourea (0.1 mol). They were mixed well with mortar-pestle and placed in small conical flask at room temperature. The mixture was then exposed to microwave irradiations for 5 min with 30 s pause at 180 W. Then 100 ml distilled water was added to the mixture and heated in microwave for 5?6 min at 270 W with 1 min pause till the precipitate dissolve. Filter the yellow solution and alkaline it with ammonia solution. Separate out the product and recrystallize with ethyl alcohol followed by diethyl ether and dried under reduced pressure.
66%	With iodine; at 100℃; for 8h;	General procedure: A mixture of thiourea (50 mmol), the corresponding acetophenone (25 mmol) and iodine (25 mmol) is stirred at 100 °C for 8 h.Then the reaction mixture is cooled, extracted with diethyl ether toremove excess of acetophenone, and then washed with aqueous sodium thiosulfate to remove excess iodine and later with cold water. The crude product is dissolved in hot water, filtered to remove sulphone, and the filtrate is basified with aqueous Na2CO3to yield the corresponding 2-amino-4-(substituted-phenyl)-1,3-thiazole. The crude product is purified by recrystallization from alcohol.
	With iodine; at 100℃; for 8h;	General procedure: A mixture of thiourea (7, 50 mmol), the corresponding acetophenone (6, 25 mmol) and iodine(25 mmol) is stirred at 100 °C for 8 h. Then the reaction mixture is cooled, extracted with diethylether to remove excess of acetophenone, and then washed with aqueous sodium thiosulfate to remove excess iodine and later with cold water. The crude product is dissolved in hot water, filtered to remove sulphone, and the filtrate is basified with aqueous Na2CO3 to yield the corresponding 2-amino-4-(substituted-phenyl)-1,3-thiazole (5). The crude product is purified by recrystallization from alcohol. The synthesis and spectral data of compounds 5a-i have been reported by us earlier [2]. The data in respect of compounds 5j-l is described here.

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 115,p. 393 - 398.
[2]Chemical and Pharmaceutical Bulletin,2007,vol. 55,p. 1014 - 1017.
[3]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 1133 - 1138.
[4]European Journal of Medicinal Chemistry,2013,vol. 66,p. 305 - 313.
[5]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1391 - 1393.
[6]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 692 - 702.
[7]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5428 - 5431.
[8]Chemical Biology and Drug Design,2017,vol. 90,p. 778 - 790.
[9]Chemical Biology and Drug Design,2018,vol. 91,p. 728 - 734.

3
[ 75-15-0 ]
[ 21344-90-1 ]
[ 74-88-4 ]
[ 153776-97-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 595 - 598.

4
[ 26340-49-8 ]
[ 201230-82-2 ]
[ 21344-90-1 ]
N-[4-(2-chlorophenyl)-2-thiazolyl]-indole-2-carboxamide [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 2421 - 2424.

5
[ 201230-82-2 ]
[ 21344-90-1 ]
[ 206196-81-8 ]
SR 27897 [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 2421 - 2424.
[2]Tetrahedron Letters,1998,vol. 39,p. 2421 - 2424.

6
[ 201230-82-2 ]
[ 21344-90-1 ]
[ 206196-82-9 ]
[ 206196-70-5 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 2421 - 2424.

7
[ 21344-90-1 ]
[ 10456-04-9 ]
methyl 2-iodoindole-1-acetate [ No CAS ]
C₂₀⁽¹¹⁾CH₁₆ClN₃O₃S [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. S81-S83.

8
[ 106-49-0 ]
[ 21344-90-1 ]
[ 528583-96-2 ]