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Chemical Structure| 443-69-6 Chemical Structure| 443-69-6
Chemical Structure| 443-69-6

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CAS No.: 443-69-6

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Product Citations

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

DOI: PubMed ID:

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

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Product Details of [ 443-69-6 ]

CAS No. :443-69-6
Formula : C8H4FNO2
M.W : 165.12
SMILES Code : C1=C(F)C=CC2=C1C(C(=O)N2)=O
MDL No. :MFCD00022795
InChI Key :GKODDAXOSGGARJ-UHFFFAOYSA-N
Pubchem ID :236566

Safety of [ 443-69-6 ]

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

Application In Synthesis [ 443-69-6 ]

* 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 [ 443-69-6 ]

[ 443-69-6 ] Synthesis Path-Downstream   1~7

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  • [ 2923-66-2 ]
  • [ 91021-10-2 ]
  • 2
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  • [ 6099-90-7 ]
  • [ 82260-63-7 ]
  • 3
  • [ 443-69-6 ]
  • [ 30065-27-1 ]
  • 2-(1H-benzimidazol-2-ylthio)-N-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetohydrazide [ No CAS ]
  • 4
  • [ 443-69-6 ]
  • [ 1077-96-9 ]
YieldReaction ConditionsOperation in experiment
51% To a solution of NaOH (1.24 g, 0.031 mol, 1.03 equiv.) in water (19 mL) heated at 50CC was added 5-Fluoroisatin (5 g, 0.03 mol, 1 equiv.). After 5 minutes, the dark- red solution was cooled to 0C and a cooled solution of sodium nitrite (2.07 g, 0.03 mol, I equiv.) in water (10 mL) was added slowly, followed by a cooled solution of (95%) (3.12 mL, 0.06 mol , 1.95 equiv.) in water (48 mL). The rate of addition was rapid such that the temperature never rose above 4C. To reduce the foaming which occurred throughout the period of stirring, a few millilitres of ether were added when necessary. After the end of addition, the cooled solution was stirred for one hour, maintaining the temperature below 4 C at all times. Then a cooled solution of SnC 1 (16.24 g, 0.072 mol, 2.4 equiv.) in HCl (35%) (24 mL) was added and the mixture was stirred for 16 h. The brown solution was filtrated and the resultion brown solid was washed with water to give a light brown solid (2.73 g, 51%); deltaEta (MeOH-￡/6) 7.25 (1H, td, J 9.10 Hz and J2.14 Hz, ArH), 7.60 (1H, dd J 9.10 Hz and 4.28 Hz, ArH), 7.74 (1H, dd J 9.10 Hz and 2.10 Hz, ArH); LC-MS-EI 183.1 (MH+, 100)
A solution of the substituted aniline (565 mL) in 6N hydrochloric acid (106 mL) was added to a suspension of 2,2,2-trichloro-1-ethoxyethanol (678 mL) and sodium sulfate (3.15 mol) in water (1.4 L) and the reaction mixture was stirred vigorously for 1 h. A solution of hydroxylamine hydrochloride (2.08 mol) in water (650 mL) was added in one portion and the reaction mixture was heated at 80 C. for 1.5 h. The reaction mixture was cooled to 10 C. and the precipitated solids were collected by filtration, washed with water, and dried to provide the amide in 91% yield. The amide was added to sulfuric acid (1.9L) and the reaction mixture was heated at 60 C. for 6 h. The reaction mixture was allowed to cool to room temperature and was cautiously poured onto ice (7 kg). The precipitated solids were collected by filtration, washed with water, and dried to provide the isatin in 61% yield. The conversion of the substituted isatins to the corresponding indazole-3-carboxylic acids is essentially the same method as described for indazole-3-carboxylic acid: Snyder, H. R., et. al. J. Am. Chem. Soc. 1952, 74, 2009. The substituted isatin (22.1 mmol) was diluted with 1 N sodium hydroxide (24 mL) and was heated at 50 C. for 30 min. The burgundy solution was allowed to cool to rt and was maintained for 1 h. The reaction mixture was cooled to 0 C. and was treated with a 0 C. solution of sodium nitrite (22.0 mmol) in water (5.5 mL). This solution was added through a pipet submerged below the surface of a vigorously stirred solution of sulfuric acid (2.3 mL) in water (45 mL) at 0 C. The addition took 15 min and the reaction was maintained for an additional 30 min. A cold (0 C.) solution of tin (II) chloride dihydrate (52.7 mmol) in concentrated hydrochloric acid (20 mL) was added to the reaction mixture over 10 min and the reaction mixture was maintained for 60 min. The precipitated solids were isolated by filtration, washed with water, and dried to give a quantitative mass balance. This material was of sufficient purity (1H NMR and LC/MS) to use in the next step without further purification. Alternatively, the acid was recrystallized from acetic acid to provide pure material.
Example 66; 5-Ethyl-2-(5-fluoro-1H-indazol-3-yl)-7,7-dimethyl-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one; In an analogous manner as described for example 3, 5-ethyl-2-(5-fluoro-1H-indazol-3-yl)-7,7-dimethyl-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one was prepared from 5,6-diamino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one (see part A, starting materials) and 5-fluoro-1H-indazole-3-carboxylic acid (prepared from 5-fluoroisatin according to WO03/035065, reference example 26 and J. Am. Chem. Soc. 1952 (74), 2009-2012). MS: M=364.3 (ESI+) 1H-NMR (400 MHz, DMSO): delta (ppm)=1.21 (t, 3H), 1.33(s, 6H), 3.78 (bq, 2H), 7.03 and 7.39 (s, 1H), 7.39 (m, 1H), 7.44 and 7.74 (s, 1H), 7.70 (m, 1H), 8.13 (m, 1H), 12.97 and 13.03 (s, 1H), 13.69 (s, 1H)
1.62 g (a) Step 1 The synthesis was performed with reference to the known literature (). Aqueous sodium hydroxide (0.500 g, 12.5 mmol, 11 mL) was heated to 50C, and added with 5-fluoroisatin (2.00 g, 12.1 mmol). The reaction mixture was stirred at 50C for 1 hour, and then cooled on ice. Aqueous sodium nitrite (0.835 g, 12.1 mmol, 4 mL) was cooled on ice, and then added dropwise to the reaction mixture. Then, the mixture was added dropwise with concentrated sulfuric acid (2.31 g, 23.6 mmol) in ice-cooled water (19 mL), and the mixture was stirred for 1 hour under ice cooling. Then, the reaction mixture was added dropwise with an ice-cooled solution of tin(II) chloride dihydrate (6.54 g, 29.0 mmol) in concentrated hydrochloric acid (9.7 mL). The reaction mixture was stirred overnight at room temperature, and then filtered, and the resulting solid was washed with water to obtain a pale brown solid (1.62 g).
Example 33; 4-([1-(4-Difluoromethoxy-benzyl)-5-fluoro-1H-indazole-3-carbonyl]-amino}-methyl)-benzoic acid; The title compound was prepared as illustrated in scheme 3 and 5.Step 1. A solution of 5-fluoro-isatin (10.0 g, 60.6 mmol) in 1N NaOH (61 mL) was stirred at 60 C. for 20 min. The solution was cooled to 3 C. and a solution of sodium nitrite (4.59 g, 66.6 mmol) in water (20 mL) was added, and the mixture stirred for 20 min. The resulting solution was added dropwise to a cooled solution of concentrated sulfuric acid (3.64 ml, 67.9 mmol) in water (130 mL) so that the temperature remained between 0 and 4 C. The mixture was stirred at 0-5 C. for 2 h, then added portionwise to a solution of SnCl2 (22.0 g, 116 mmol) in concentrated HCl (46 mL). The mixture was left for 5 hours, upon which crystallization took place. The crystals were filtered off, washing with water, to yield 5-fluoro-1H-indazole-3-carboxylic acid as a white solid (9.76 g). The raw material was then dissolved in tetrahydrofuran (100 mL) and treated with carbonyldiimidazole (CDI, 9.82 g, 60.6 mmol). The mixture was warmed to reflux and stirred for 2 hours. EtOH (100 mL) was then added, and the mixture stirred at reflux for further 5 hours. The volatiles were evaporated and the residue redissolved in warm ethyl acetate. The organic solution was washed with 1N HCl, and then with water, dried with sodium sulphate and evaporated. The raw material was purified by flash chromatography (heptane/ethyl acetate 1:1, followed by a second chromatography with dichloromethane/diethyl ether 9:1) to yield 5-fluoro-1H-indazole-3-carboxylic acid ethyl ester as an off-white solid, 6.22 g (49.3%).

  • 5
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  • [ 1131-18-6 ]
  • [ 50607-30-2 ]
  • 5-fluoro-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
  • [ 443-69-6 ]
  • [ 4149-06-8 ]
  • [ 347-84-2 ]
  • 5-fluoro-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
91% 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
  • [ 2343-22-8 ]
  • [ 443-69-6 ]
YieldReaction ConditionsOperation in experiment
87% With iodine pentoxide; In dimethyl sulfoxide; at 80℃; General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.
 

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