Isatin | Indoline-2,3-dione | Indolines

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Quality Control of Isatin Purity: 98% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Citations Show More

Metabolism-Guided Selective Androgen Receptor Antagonists: Design, Synthesis, and Biological Evaluation for Activity against Enzalutamide-Resistant Prostate Cancer

Hwang, Dong-Jin ; He, Yali ; Ponnusamy, Suriyan ; Thiyagarajan, Thirumagal ; Mohler, Michael L. ; Narayanan, Ramesh , et al.

DOI: 10.1021/acs.jmedchem.2c01858 PubMed ID: 36825758 JMC,2023,66(5):3372-3392.

Abstract: A major challenge for new drug discovery in the area of androgen receptor (AR) antagonists lies in predicting the druggable properties that will enable small mols. to retain their potency and stability during further studies in vitro and in vivo. Indole (compound 8) is a first-in-class AR antagonist with very high potency (IC50 = 0.085 μM) but is metabolically unstable. During the metabolic studies described herein, we synthesized new small mols. that exhibit significantly improved stability while retaining potent antagonistic activity for an AR. This structure-activity relationship (SAR) study of more than 50 compounds classified with three classes (Class I, II, and III) and discovered two compounds (32c and 35i) that are potent AR antagonists (e.g., IC50 = 0.021 μM, T1/2 = 120 min for compound 35i). The new antagonists exhibited improved in vivo pharmacokinetics (PK) with high efficacy antiandrogen activity in Hershberger and antiandrogen Enz-Res tumor xenograft models that overexpress AR (LNCaP-AR).

Purchased from AmBeed: 91-56-5 ; 915087-33-1

The evaluation of isatin analogues as inhibitors of monoamine oxidase

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

DOI: 10.1111/cbdd.14304 PubMed ID: 37500571 Chem. Biol. Drug Des.,2023,102(5):1067-1074.

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

Purchased from AmBeed: 6341-92-0 ; 91-56-5 ; 1127-59-9 ; 611-09-6 ; 7477-63-6 ; 6344-05-4 ; 443-69-6 ; 87-48-9 ; 39603-24-2 ; 608-05-9 ; 17630-76-1 ; 20205-43-0 ; 131609-60-4 ; 150560-58-0 ; 57816-97-4

Product Details of Isatin

CAS No. :	91-56-5
Formula :	C₈H₅NO₂
M.W :	147.13
SMILES Code :	O=C1NC2=C(C=CC=C2)C1=O
Synonyms :	Indoline-2,3-dione
MDL No. :	MFCD00005718
InChI Key :	JXDYKVIHCLTXOP-UHFFFAOYSA-N
Pubchem ID :	7054

Safety of Isatin

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of Isatin

* 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 [ 91-56-5 ]
Downstream synthetic route of [ 91-56-5 ]

[ 91-56-5 ] Synthesis Path-Upstream 1~4

1
[ 91-56-5 ]
[ 20198-19-0 ]
[ 86-96-4 ]

References: [1] Gazzetta Chimica Italiana, 1956, vol. 86, p. 119,125.

2
[ 91-56-5 ]
[ 513-86-0 ]
[ 1245-13-2 ]

References: [1] Russian Chemical Bulletin, 2010, vol. 59, # 4, p. 724 - 732.
[2] Journal of the American Chemical Society, 1942, vol. 64, p. 1897,1898.

3
[ 91-56-5 ]
[ 4091-39-8 ]
[ 1245-13-2 ]

References: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2705,2707.

4
[ 91-56-5 ]
[ 431-03-8 ]
[ 1245-13-2 ]

References: [1] Chemistry - A European Journal, 2004, vol. 10, # 15, p. 3685 - 3696.

[ 91-56-5 ] Synthesis Path-Downstream 1~35

1
[ 4225-92-7 ]
[ 91-56-5 ]
3-hydroxy-2-mesityl-quinoline-4-carboxylic acid [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 259,268.

2
[ 391-12-8 ]
[ 91-56-5 ]
[ 1150-98-7 ]

References: [1]Journal of Pharmaceutical Sciences,1980,vol. 69,p. 1235 - 1237.

3
[ 20197-92-6 ]
[ 91-56-5 ]
2,3-dimethoxyindolo[2,1-b]quinazolin-6,12-dione [ No CAS ]

References: [1]Synthesis,2009,p. 3642 - 3648.
[2]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2303 - 2307.
[3]Acta Pharmacologica Sinica,2010,vol. 31,p. 259 - 264.
[4]Heterocyclic Communications,2015,vol. 21,p. 67 - 71.

4
[ 1631-26-1 ]
[ 600-21-5 ]
[ 91-56-5 ]
4-benzyl-1,6-dimethylpyrrolidino[3,4-c]pyrrole-2-spiro-3'-(2-oxindole)-3,5-dione [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 413 - 418.

5
[ 2895-21-8 ]
[ 91-56-5 ]
[ 667914-16-1 ]

References: [1]Molecules,2008,vol. 13,p. 831 - 840.
[2]Synthesis,2007,p. 829 - 834.

6
[ 91-56-5 ]
[ 132898-96-5 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6704 - 6715.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 419 - 430.

7
[ 700-06-1 ]
[ 487-89-8 ]
[ 91-56-5 ]

References: [1]Synlett,2008,p. 2023 - 2027.

8
[ 91-56-5 ]
[ 1194-22-5 ]
[ 109-77-3 ]
[ 1204748-06-0 ]

References: [1]ACS Combinatorial Science,2013,vol. 15,p. 530 - 534.
[2]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 1266 - 1270.
[3]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 967 - 972.

9
[ 91-56-5 ]
[ 126-81-8 ]
[ 1194-22-5 ]
[ 1246222-44-5 ]

References: [1]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 967 - 972.

10
[ 608-32-2 ]
[ 91-56-5 ]
[ 1097635-50-1 ]

References: [1]Heterocycles,2008,vol. 75,p. 2745 - 2759.

11
[ 1131-18-6 ]
[ 52851-41-9 ]
[ 91-56-5 ]
[ 1309588-51-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With toluene-4-sulfonic acid; In ethanol; water; at 80.0℃;	A solution of 5-aminopyrazole 5a-c (0.1 mmol), beta-diketone 3 (0.1 mmol) and isatin 6 (0.1 mmol) in H2O/EtOH [5:1 (v/v))] and a catalytic amounts of PTSA (0.1 g) was heated at 80 C (water bath) for 6-12 h. Then, the reaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol.

References: [1]Tetrahedron Letters,2011,vol. 52,p. 2664 - 2666.

12
[ 91-56-5 ]
[ 5467-57-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4629 - 4635.
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 993 - 1013.
[3]Patent: CN109467549,2019,A .

13
[ 91-56-5 ]
[ 1194-22-5 ]
[ 105-34-0 ]
methyl 7'-amino-4'-hydroxy-2'-methyl-2-oxospiro[indoline-3,5'-pyrano[2,3-d]pyrimidine]-6'-carboxylate [ No CAS ]

References: [1]ACS Combinatorial Science,2013,vol. 15,p. 530 - 534.

14
[ 27037-34-9 ]
[ 91-56-5 ]
7-methoxy-3-(2-oxoindolin-3-ylidene)quinoline-2,4(1H,3H)-dione [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2015,vol. 52,p. 492 - 496.

15
[ 20197-92-6 ]
[ 91-56-5 ]
[ 1204648-94-1 ]

References: [1]Heterocyclic Communications,2015,vol. 21,p. 67 - 71.

16
[ 67442-07-3 ]
[ 91-56-5 ]
2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-methoxy-N-methylacetamide [ No CAS ]

References: [1]Green Chemistry,2015,vol. 17,p. 4194 - 4197.

17
[ 91-56-5 ]
[ 20876-36-2 ]

References: [1]Archiv der Pharmazie,2015,vol. 348,p. 715 - 729.

18
[ 91-56-5 ]
[ 78364-55-3 ]
6-fluoro-2-(2-(2-oxoindolin-3-ylidene)hydrazino)benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With acetic acid; In ethanol;Reflux;	General procedure: 6-Fluoro-2-(2-(5-(un)substituted-2-oxoindolin-3-ylidene)hydrazino)benzothiazoles 5a-c. General Procedure C. A mixture of compound 2 (0.183 g, 0.001 mol), the appropriate isatin (0.001 mol) and glacial acetic acid (0.1 mL) in ethanol (20 mL) was heated at reflux temperature for 4-6 h. The precipitated yellow to orange solid was collected by filtration, washed with ethanol, dried and crystallized from methanol to yield compounds 5a-c.

References: [1]Chinese Chemical Letters,2015,vol. 26,p. 1522 - 1528.

19
[ 91-56-5 ]
[ 93783-15-4 ]
[ 132898-96-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With chlorosulfonic acid; at 5 - 70℃;	1H-indole-2,3-dione (4.41 g, 30 mmol) was added in portions into chlorosulfonic acid (34.8 g, 300 mmol) below 5 C. The reaction mixture was stirred for another 0.5 h at the same temperature and then the reaction temperature was slowly raised to 70 C and maintained for 3 h. The mixture was cooled and poured into ice, standed still 0.5 h in the ice water, filtrated and the solid was washed with cold water, dried in vacuum oven to afford compound 3 (6.34 g, 70 %). White solid, m.p.: 165-166 C. 1H NMR (400 MHz, CD3COCD3, TMS): delta 8.39(d, J = 2.0 Hz, 1H), 8.23 (dd, J = 8.5, 2.0 Hz, 1H), 7.46 (d, J =8.5 Hz, 1H), 3.29 (s, 1H). IR (KBr, numax, cm-1): 3363, 2963,1767, 1615, 1475, 1359, 1296, 1167, 1124, 1067, 960, 838,714, 595, 511. HR-MS (ESI): Calcd for C8H4NO3SCl3 [M-H]-: 297.8899; found: 297.8897.

References: [1]Asian Journal of Chemistry,2015,vol. 27,p. 2959 - 2963.

20
[ 91-56-5 ]
[ 57297-29-7 ]
[ 459796-19-1 ]

References: [1]Organic Letters,2016,vol. 18,p. 2942 - 2945.

21
[ 1131-18-6 ]
[ 91-56-5 ]
[ 50607-30-2 ]
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 ]

References: [1]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 1578 - 1583.

22
[ 6972-82-3 ]
[ 91-56-5 ]
6-amino-1-methyl-5-[(3Z)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]amino}pyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In ethanol;Reflux;	General procedure: A mixture of 5,6-diamino-1-substituted-uracils (3) (1.00 mmol) andisatin (1.00 mmol) in ethanol (20 mL) in the presence of TEA as abase was heated under reflux for 4?5 h. The resulting precipitate wasfiltered hot, washed with ethanol and crystallised from DMF/ethanol(1:3) to afford the desired compounds 15?17.6-Amino-1-methyl-5-[(3Z)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]amino}pyrimidine-2,4(1H, 3H)-dione (15): Yield 85percent; m.p. > 300 °C;IR (numax, cm?1) KBr: 3349, 3309, 3260, 3146 (NH2 and NH), 3054 (CHAr), 2846 (CH aliph.), 1693, 1643 (C=O), 1575 (C=C); 1H NMR (400MHz, DMSO-d6) delta 11.78 (s, 1H, NH), 10.54 (s, 1H, NH), 8.22?8.20 (d,1H, ArH), 7.63?7.56 (m, 2H, ArH), 7.42?7.38 (m, 1H, ArH), 6.11 (s,2H, NH2), 3.56 (s, 3H, CH3); 13C NMR (100 MHz, DMSO-d6) delta 28.7,96.1, 120.2, 128.1, 136.5, 143.2, 146.0, 149.3, 151.2, 158.0, 159.4, 160.8,171.4; MS m/z (percent) 285 ([M]+,1.13), 156 (100), 139 (46), 98 (15), 84(21), 57 (51); Anal. calcd for C13H11N5O3: C, 54.74; H, 3.89; N, 24.55;found: C, 54.91; H, 3.94; N, 24.67percent.

References: [1]Journal of Chemical Research,2016,vol. 40,p. 771 - 777.

23
[ 91-56-5 ]
[ 24629-25-2 ]
C₂₄H₃₆N₂O₂ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4829 - 4833.
Angew. Chem.,2017,vol. 129,p. 4907 - 4911,5.

24
[ 91-56-5 ]
[ 24629-25-2 ]
C₁₄H₁₈N₂O₂ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4829 - 4833.
Angew. Chem.,2017,vol. 129,p. 4907 - 4911,5.

25
[ 91-56-5 ]
[ 57297-29-7 ]
2-(4,6-dicyclopropyl-1,3,5-triazin-2-yl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 20℃; for 5h;	The specific steps are as follows: adding blush (44.1 mg, 0.3 mmol) to the pressure tube, cyclopropyl-substituted hydrazine hydrochloride (108.5 mg,0.9 mmol), CuI (5.7 mg, 0.03 mmol) and potassium phosphate (381.6 mg, 1.8 mmol), added to 3 mL of DMSO, magnetic at room temperatureAfter stirring for 5 hours, the reaction mixture was extracted with methylene chloride.After that, the solvent is distilled off under reduced pressure to obtain a crude product, and the crude product is subjected to column separation using dichloromethane/petroleum ether = 1:20 (V/V) as eluent.Purification is the desired product, the product is a yellow solid with a yield of 34percent.

References: [1]Patent: CN108558782,2018,A .Location in patent: Paragraph 0035.
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4223 - 4226.

26
[ 40711-33-9 ]
[ 91-56-5 ]
[ 109-77-3 ]
C₁₇H₁₃N₅O₄ [ No CAS ]

References: [1]New Journal of Chemistry,2018,vol. 42,p. 17279 - 17290.

27
[ 91-56-5 ]
[ 4498-72-0 ]