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Chemical Structure| 17630-76-1 Chemical Structure| 17630-76-1

Structure of 5-Chloroisatin
CAS No.: 17630-76-1

Chemical Structure| 17630-76-1

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CAS No.: 17630-76-1

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Product Citations

Product Citations

Prinsloo, Izak F. ; Petzer, Jacobus P. ; Cloete, Theunis T. ; Petzer, Anel ;

Abstract: The small mol., isatin, is a well-known reversible inhibitor of the monoamine oxidase (MAO) enzymes with IC50 values of 12.3 and 4.86μM for MAO-A and MAO-B, resp. While the interaction of isatin with MAO-B has been characterized, only a few studies have explored structure-activity relationships (SARs) of MAO inhibition by isatin analogs. The current study therefore evaluated a series of 14 isatin analogs as in vitro inhibitors of human MAO-A and MAO-B. The results indicated good potency MAO inhibition for some isatin analogs with five compounds exhibiting IC50 < 1μM. 4-Chloroisatin (1b) and 5-bromoisatin (1f) were the most potent inhibitors with IC50 values of 0.812 and 0.125μM for MAO-A and MAO-B, resp. These compounds were also found to be competitive inhibitors of MAO-A and MAO-B with Ki values of 0.311 and 0.033μM, resp. Among the SARs, it was interesting to note that C5-substitution was particularly beneficial for MAO-B inhibition. MAO inhibitors are established drugs for the treatment of neuropsychiatric and neurodegenerative disorders, while potential new roles in prostate cancer and cardiovascular disease are being investigated.

Keywords: competitive ; inhibition ; isatin ; monoamine oxidase ; structure-activity relationship

Alternative Products

Product Details of [ 17630-76-1 ]

CAS No. :17630-76-1
Formula : C8H4ClNO2
M.W : 181.58
SMILES Code : C1=C(Cl)C=CC2=C1C(C(=O)N2)=O
MDL No. :MFCD00014567
InChI Key :XHDJYQWGFIBCEP-UHFFFAOYSA-N
Pubchem ID :87203

Safety of [ 17630-76-1 ]

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

Computational Chemistry of [ 17630-76-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 47.17
TPSA ?

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

46.17 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.1
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

1.27
Log Po/w (WLOGP)?

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

0.9
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.

0.75
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

2.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.24

Water Solubility

Log S (ESOL):?

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

-2.14
Solubility 1.33 mg/ml ; 0.00731 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.

-1.84
Solubility 2.63 mg/ml ; 0.0145 mol/l
Class?

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

Very 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

-3.39
Solubility 0.0735 mg/ml ; 0.000405 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

 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

 No
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.

-6.51 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

 1.0
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

1.0 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)

 1.47

Application In Synthesis of [ 17630-76-1 ]

* 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 [ 17630-76-1 ]

[ 17630-76-1 ] Synthesis Path-Downstream   1~11

  • 1
  • ammonium chloride [ No CAS ]
  • [ 17630-76-1 ]
  • [ 101335-11-9 ]
  • [ 365525-95-7 ]
YieldReaction ConditionsOperation in experiment
With magnesium; In tetrahydrofuran; diethyl ether; Preparation 9 5-Chloro-3-(2-chloro-4-fluorophenyl)-3-hydroxyindolin-2-one, Compound II.10 0.44 g of a 60% dispersion of sodium hydride in oil is added at -40 C. to a cooled suspension of 2 g of 5-chloroindolin-2,3-dione in 60 ml of tetrahydrofuran and the reaction mixture is stirred at 0 C. for 15 minutes. 0.45 g of magnesium and 4.23 g of <strong>[101335-11-9]2-chloro-4-fluoro-1-iodobenzene</strong> in 18 ml of diethyl ether are stirred at reflux for 3 hours. The solution thus obtained is slowly added at -60 C. to the reaction mixture. The reaction mixture is stirred for 30 minutes at 20 C. and a saturated aqueous ammonium chloride solution is added. Extraction is carried out with ethyl acetate, the organic phase is dried over anhydrous sodium sulphate and the solvents are evaporated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, elution being carried out with dichloromethane and then with a 95/5 (v/v) dichloromethane/methanol mixture. The solid obtained is crystallized from n-pentane; M.p.=239 C. In the same way, 5-chloro-3-(2,5-dimethoxyphenyl)-3-hydroxyindolin-2-one, compound II,11;
  • 2
  • [ 20197-92-6 ]
  • [ 17630-76-1 ]
  • [ 1268269-39-1 ]
  • 3
  • [ 17630-76-1 ]
  • [ 102735-84-2 ]
  • 4
  • [ 17630-76-1 ]
  • [ 73458-39-6 ]
  • (N,N'E,N,N'Z)-N,N′-(5-chloroindoline-2,3-diylidene)bis(5-nitrobenzo[d]thiazol-2-amine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With acetic acid; In methanol;Reflux; A 10mmol solution of 5-nitro-2-aminobenzothiazole in 30 mlmethanolwas added drop wise to a 5 mmol solution of 5-chloroisatin dissolvedin 30 ml methanol. The reaction mixture was refluxed for 6 hin the presence of catalytic amount of glacial acetic acid (1-3 drops)which led to the isolation of microcrystalline solid product (Scheme 1).The productwas filtered,washed several timeswithmethanol and finallydried in vacuum over anhydrous calcium chloride.
  • 5
  • [ 1131-18-6 ]
  • [ 17630-76-1 ]
  • [ 50607-30-2 ]
  • 5-chloro-3'-methyl-1'-phenyl-6',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b][1,6]naphthyridine]-2,5'(1'H)-dione [ No CAS ]
  • 6
  • [ 4149-06-8 ]
  • [ 347-84-2 ]
  • [ 17630-76-1 ]
  • 5-chloro-6'-(4-fluorophenyl)-2',5'-diphenyl-1',2'-dihydrospiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,3'(7'H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid; In water; at 90℃; for 5h;Green chemistry; General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.
  • 7
  • [ 17630-76-1 ]
  • [ 57297-29-7 ]
  • 4-chloro-2-(4,6-dicyclopropyl-1,3,5-triazin-2-yl)aniline [ No CAS ]
  • 8
  • [ 17630-76-1 ]
  • [ 873-95-0 ]
  • 3-(2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-5-chloro-3-hydroxyindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In water; at 80℃; for 6h; A solution of 200?mg (1.10?mmol) of 5-chloroisatin (1c), 153?mg (1.10?mmol) of <strong>[873-95-0]3-amino-5,5-dimethylcyclohex-2-enone</strong> (2b) was heated to 80 C in H2O for 6?h. After the TLC indicated the complete consumption of 5-chloroisatin (1c), the reaction mixture was extracted with ethyl acetate three times. The combined organic layer was dried over Na2SO4 and evaporated on rotatory evaporator to provide light yellow solid which was purified by silica gel column chromatography using hexane:ethyl acetate (2:8) as an eluent to provide 7 as white solid (239?mg).
68% In water; at 80℃;Green chemistry; General procedure: A mixture of isatin (1a) (0.3 gm, 2.0 mmol) and enaminone (2a) (0.333 gm,2.4 mmol) in 10 mL of water was heated in an oil bath at 80C for 9 hours. Initially,orange-colored reaction mixture appeared to be homogeneous but with the progress ofthe reaction, yellow color solid precipitated out. After the TLC indicated the completeconsumption of starting materials, the precipitated solid was filtered off. The solid wasthen dried under vacuum and purified by silica gel column chromatography by using EA: hexane (8:2) as an eluent to provide the desired product.
  • 9
  • [ 17630-76-1 ]
  • [ 145091-87-8 ]
  • [ 109-77-3 ]
  • [ 1558716-60-1 ]
YieldReaction ConditionsOperation in experiment
83% With 2-amino-2-hydroxymethyl-1,3-propanediol; In ethanol; at 20℃; for 5h; General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.
  • 10
  • [ 1193314-86-1 ]
  • [ 17630-76-1 ]
  • [ 1193314-23-6 ]
 

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