5-(4-Isopropylphenyl)-1,3,4-thiadiazol-2-amine

Cat.NO.:A219722 Purity:95%

Product Details of [ 100987-89-1 ]

CAS No. :	100987-89-1
Formula :	C₁₁H₁₃N₃S
M.W :	219.31
SMILES Code :	NC1=NN=C(C2=CC=C(C(C)C)C=C2)S1
MDL No. :	MFCD02032690
InChI Key :	QEKWMJDRQOKJJS-UHFFFAOYSA-N
Pubchem ID :	879437

Safety of [ 100987-89-1 ]

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

Computational Chemistry of [ 100987-89-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	11
Fraction Csp3	0.27
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	64.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	80.04 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.23
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	2.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.92
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.	2.12
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	3.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.69

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.38
Solubility	0.0913 mg/ml ; 0.000416 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.	-4.15
Solubility	0.0156 mg/ml ; 0.0000711 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	-3.91
Solubility	0.027 mg/ml ; 0.000123 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.	-5.64 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)	2.59

Application In Synthesis of [ 100987-89-1 ]

* 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 [ 100987-89-1 ]

[ 100987-89-1 ] Synthesis Path-Downstream 1~9

1
[ 15781-70-1 ]
[ 100987-89-1 ]
[ 141421-46-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

2
[ 13816-33-6 ]
[ 79-19-6 ]
[ 100987-89-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

3
[ 100987-89-1 ]
[ 101367-13-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

4
[ 100987-89-1 ]
[ 101302-35-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

5
[ 100987-89-1 ]
[ 141421-90-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

6
[ 100987-89-1 ]
[ 141421-68-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

7
[ 100987-89-1 ]
[ 141422-10-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 357 – 363.

8
[ 122-03-2 ]
[ 100987-89-1 ]

References: [1]Catalysis Letters,2018,vol. 148,p. 3486 – 3491.

9
[ 3811-20-9 ]
[ 100987-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	With iodosylbenzene; dihydrogen peroxide; acetic acid; In dimethyl sulfoxide; at 60℃; for 4.0h;Green chemistry;	General procedure: To a mixture of thiosemicarbazide (3, 0.5mmol), sodiumacetate (0.5mmol), aldehyde (2, 0.5mmol), 3mL of solvent(vH2O:vEtOH=1:1) was successively added into the tube andstirred for 15min at room temperature. After the reactionwas completed, the solvent was evaporated under reducedpressure and the residue was redissolved in DMSO (3mL),followed by addition of acetic acid (2 equiv), PhI (10mol%)and H2O2(2 equiv) in sequence, and then stirred at 60Cfor 4h (monitored by TLC). After allowing to attain roomtemperature, the saturated solution of Na2S2O3(5mL) wasadded to the reaction mixture in order to quench and then themixture was extracted with ethyl acetate (3 × 10mL). Thecombined organic layer was dried over anhydrous MgSO4and concentrated. Finally, the residue was purified by flashcolumn chromatography on silica gel using a mixture of ethylacetate and petroleum ether as eluent to give the products.

References: [1]Catalysis Letters,2018,vol. 148,p. 3486 – 3491.

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5-(4-Isopropylphenyl)-1,3,4-thiadiazol-2-amine

Product Details of [ 100987-89-1 ]

Safety of [ 100987-89-1 ]

Computational Chemistry of [ 100987-89-1 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 100987-89-1 ]

[ 100987-89-1 ] Synthesis Path-Downstream 1~9

Details

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