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Hwang, Dong-Jin ; He, Yali ; Ponnusamy, Suriyan , et al. DOI: PubMed ID:

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).

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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 [ 91-56-5 ]

CAS No. :91-56-5 MDL No. :MFCD00005718
Formula : C8H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JXDYKVIHCLTXOP-UHFFFAOYSA-N
M.W : 147.13 Pubchem ID :7054
Synonyms :
Indoline-2,3-dione
Chemical Name :2,3-Indolinedione

Calculated chemistry of [ 91-56-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
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 : 42.16
TPSA : 46.17 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.83
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 0.25
Log Po/w (MLOGP) : 0.17
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.68
Solubility : 3.08 mg/ml ; 0.021 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 6.1 mg/ml ; 0.0415 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.258 mg/ml ; 0.00175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 91-56-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 91-56-5 ]

* 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   1~38

  • 1
  • [ 67-56-1 ]
  • [ 91-56-5 ]
  • [ 43120-28-1 ]
Reference: [1] Patent: WO2015/25025, 2015, A1, . Location in patent: Page/Page column 106; 107
  • 2
  • [ 91-56-5 ]
  • [ 4743-17-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1886, vol. &lt;2&gt; 33, p. 36
  • 3
  • [ 91-56-5 ]
  • [ 598-31-2 ]
  • [ 117-57-7 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1982, vol. 18, # 8, p. 871 - 872[2] Khimiya Geterotsiklicheskikh Soedinenii, 1982, vol. 18, # 8, p. 1130
  • 4
  • [ 91-56-5 ]
  • [ 117-57-7 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 22, p. 482
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 2730,2732
  • 5
  • [ 592-20-1 ]
  • [ 91-56-5 ]
  • [ 117-57-7 ]
Reference: [1] Journal of Pharmacology and Experimental Therapeutics, 1949, vol. 95, p. 185,186
  • 6
  • [ 61-70-1 ]
  • [ 91-56-5 ]
  • [ 97207-47-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. &lt;2&gt;128, p. 1,23
  • 7
  • [ 91-56-5 ]
  • [ 61-70-1 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 6, p. 1373 - 1376
[2] Organic Letters, 2016, vol. 18, # 20, p. 5232 - 5235
[3] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
[4] Tetrahedron Letters, 2018, vol. 59, # 37, p. 3409 - 3412
[5] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51
  • 8
  • [ 91-56-5 ]
  • [ 20876-36-2 ]
Reference: [1] Archiv der Pharmazie, 2015, vol. 348, # 10, p. 715 - 729
  • 9
  • [ 91-56-5 ]
  • [ 20780-76-1 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 11, p. 2089 - 2092
[2] Heterocyclic Communications, 2003, vol. 9, # 1, p. 31 - 34
[3] Organic Letters, 2009, vol. 11, # 13, p. 2844 - 2847
[4] Inorganic Chemistry, 2013, vol. 52, # 23, p. 13779 - 13790
[5] Chemische Berichte, 1924, vol. 57, p. 1773
[6] Journal of the Chemical Society, 1925, vol. 127, p. 773[7] Journal of the Chemical Society, 1926, p. 644
[8] Chemische Berichte, 1924, vol. 57, p. 2116
[9] Journal of the Chemical Society, 1926, p. 2908
  • 10
  • [ 7647-01-0 ]
  • [ 91-56-5 ]
  • [ 7790-99-0 ]
  • [ 20780-76-1 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 1773
[2] Chemische Berichte, 1924, vol. 57, p. 2116
[3] Journal of the Chemical Society, 1926, p. 2908
[4] Journal of the American Chemical Society, 1932, vol. 54, p. 1917
[5] Chemische Berichte, 1924, vol. 57, p. 1773
[6] Chemische Berichte, 1924, vol. 57, p. 2116
[7] Journal of the Chemical Society, 1926, p. 2908
[8] Journal of the American Chemical Society, 1932, vol. 54, p. 1917
  • 11
  • [ 91-56-5 ]
  • [ 7790-99-0 ]
  • [ 64-19-7 ]
  • [ 20780-76-1 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 1773
[2] Chemische Berichte, 1924, vol. 57, p. 2116
[3] Journal of the Chemical Society, 1926, p. 2908
[4] Journal of the American Chemical Society, 1932, vol. 54, p. 1917
[5] Chemische Berichte, 1924, vol. 57, p. 1773
[6] Chemische Berichte, 1924, vol. 57, p. 2116
[7] Journal of the Chemical Society, 1926, p. 2908
[8] Journal of the American Chemical Society, 1932, vol. 54, p. 1917
  • 12
  • [ 91-56-5 ]
  • [ 20198-19-0 ]
  • [ 86-96-4 ]
Reference: [1] Gazzetta Chimica Italiana, 1956, vol. 86, p. 119,125
  • 13
  • [ 101080-38-0 ]
  • [ 20780-74-9 ]
  • [ 91-56-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3715 - 3723
  • 14
  • [ 91-56-5 ]
  • [ 3597-63-5 ]
Reference: [1] Angewandte Chemie, 1980, vol. 92, # 3, p. 196 - 197
[2] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 7, p. 603 - 605
  • 15
  • [ 91-56-5 ]
  • [ 3597-63-5 ]
Reference: [1] Patent: US4297491, 1981, A,
[2] Patent: US4297491, 1981, A,
  • 16
  • [ 141-82-2 ]
  • [ 91-56-5 ]
  • [ 15733-89-8 ]
YieldReaction ConditionsOperation in experiment
97.3% for 6 h; Reflux; Large scale 400 kg of recovered glacial acetic acid was placed in a 1000 L reactor and 100 kg of isatin, 160 kg of malonic acid, and 15 kg of sodium acetate were added under stirring. The mixture was heated to reflux and refluxed for 6 hours. After the reaction is completed, the acetic acid is distilled off under reduced pressure. 300 kg of deionized water are added to stir the crystals. The filtered solids are first washed with cold 30 kg glacial acetic acid and then rinsed with cold 30 kg methanol to obtain 2-hydroxy-. 4-Carboxyquinoline wet product, after filtering and drying at 45-70°C for 24 hours,125 kg of 2-hydroxy-4-carboxyquinoline was obtained with a yield of 97.3percent and a liquid phase purity of 99.6percent.
40% for 16 h; Reflux A stirred suspension of isatin, also called 1H-indole-2,3-dione, available from Sigma-Aldrich, (3.80 g, 25 mmol) and malonic acid (8.06 g, 77 mmol) in acetic acid (150 ml) was refluxed for 16 h. Acetic acid was removed under reduced pressure, the residue was suspended in water (150 ml), filtered and washed with water (100 ml) to give a brown solid. The solid was stirred in NaHCO3 saturated aqueous solution (200 ml) and the insoluble material was filtered off. The filtrate was acidified to pH 1-2 withconcentrated HCl and the precipitate was filtered, washed with water and dried to obtainthe desired product as a grey solid (2.2 g, 11.6 mmol, Yield 40percent). 1H NMR (500 MHz; d6-DMSO) δ 6.87 (5, 1H), 7.23 (ddd, 1H, J= 1.2 Hz, J= 7.2 Hz, J=8.3 Hz), 7.41 (dd, 1H, J= 0.7 Hz, J= 8.3 Hz), 7.55 (ddd, 1H, J= 1.4 Hz, J= 7.2 Hz, J=8.4 Hz), 8.15 (dd, 1H, J= 1.2 Hz, J= 8.3 Hz), 12.13 (brs, 1H) ppm. Purity by LCMS (UV Chromatogram, 190-450nm) 90percent, rt = 2.96 min m/z 190 (M+H)+
40% for 16 h; Reflux Preparation 10
2-hydroxyquinoline-4-carboxylic acid
A stirred suspension of isatin, also called 1H-indole-2,3-dione, available from Sigma-Aldrich, (3.80 g, 25 mmol) and malonic acid (8.06 g, 77 mmol) in acetic acid (150 ml) was refluxed for 16 h.
Acetic acid was removed under reduced pressure, the residue was suspended in water (150 ml), filtered and washed with water (100 ml) to give a brown solid.
The solid was stirred in NaHCO3 saturated aqueous solution (200 ml) and the insoluble material was filtered off.
The filtrate was acidified to pH 1-2 with concentrated HCl and the precipitate was filtered, washed with water and dried to obtain the desired product as a grey solid (2.2 g, 11.6 mmol, Yield 40percent).
1H NMR (500 MHz; d6-DMSO) δ 6.87 (s, 1H), 7.23 (ddd, 1H, J=1.2 Hz, J=7.2 Hz, J=8.3 Hz), 7.41 (dd, 1H, J=0.7 Hz, J=8.3 Hz), 7.55 (ddd, 1H, J=1.4 Hz, J=7.2 Hz, J=8.4 Hz), 8.15 (dd, 1H, J=1.2 Hz, J=8.3 Hz), 12.13 (brs, 1H) ppm.
Purity by LCMS (UV Chromatogram, 190-450 nm) 90percent, rt=2.96 min, m/z 190 (M+H)+
Reference: [1] Patent: CN108101842, 2018, A, . Location in patent: Paragraph 0021; 0023
[2] Synthetic Communications, 2005, vol. 35, # 17, p. 2243 - 2250
[3] Patent: WO2013/153357, 2013, A1, . Location in patent: Page/Page column 44
[4] Patent: US2015/45354, 2015, A1, . Location in patent: Paragraph 0271-0274
[5] Chemische Berichte, 1914, vol. 47, p. 358
[6] Journal of the Chemical Society, 1926, p. 2908
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1727
  • 17
  • [ 91-56-5 ]
  • [ 15733-89-8 ]
Reference: [1] Helvetica Chimica Acta, 1957, vol. 40, p. 499
[2] Archiv der Pharmazie (Weinheim, Germany), 1899, vol. 237, p. 687
  • 18
  • [ 91-56-5 ]
  • [ 5467-57-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4629 - 4635
  • 19
  • [ 91-56-5 ]
  • [ 60434-13-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 42, p. 7372 - 7386
  • 20
  • [ 91-56-5 ]
  • [ 20870-79-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7349 - 7353
[2] Letters in Organic Chemistry, 2011, vol. 8, # 7, p. 526 - 530
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7440 - 7443
[4] Archiv der Pharmazie, 2015, vol. 348, # 10, p. 715 - 729
  • 21
  • [ 91-56-5 ]
  • [ 4692-98-2 ]
YieldReaction ConditionsOperation in experiment
77% With N-Bromosuccinimide In acetonitrile at 20℃; for 528 h; The reaction was carried out in a round-bottom flask fittedwith a magnetic stirrer bar and a rubber septum with aneedle as vent. To a solution of 1.00 g isatin (3, 6.8 mmol)in 95 cm3 acetonitrile, a solution of 6.05 g NBS (34 mmol)in 40 cm3 acetonitrile was added at temperature 0 C. Nextreaction was continued for 22 days at ambient temperature,with access to air. The separated solid was collected byfiltration and washed with acetonitrile (2 9 10 cm3). Thepure product was obtained as a yellow solid in 77 percent yield.
Reference: [1] Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1723 - 1731
  • 22
  • [ 91-56-5 ]
  • [ 5463-29-6 ]
Reference: [1] Chemische Berichte, 1914, vol. 47, p. 358
  • 23
  • [ 91-56-5 ]
  • [ 6943-17-5 ]
Reference: [1] Patent: CN106146410, 2016, A,
  • 24
  • [ 91-56-5 ]
  • [ 611-09-6 ]
YieldReaction ConditionsOperation in experiment
91% at 0℃; for 1 h; A solution of NaNO3 (5.78 g, 0.068 mol) in concentrated H2SO4 (100 mL) was added drop wise, with stirring, to a solution of isatin 3h (10.0 g, 0.068 mol) in concentrated H2S04 (120 mL) for a period of 1 h at 0 °C. Then the reaction mixture was poured into ice water (750 mL), the precipitate was collected by filtration and washed with water to give 22a. Yield 11. 88 g, 91percent.
90% at 5℃; for 3 h; A mixture of compound 10 (10g, 0.068mol) and 100ml of H2SO4 (98percent) was iced to 5°C, then Sodium nitrate(6g, 0.071mol) was added slowly to ensure the temperature was low 5°C. The mixture was continued to stir 3h after the sodium acetate added. The mixture was poured to ice water and the yellow solid precipitate. The precipitate was filtered out and dried to get 11.75g of yellow solid with a yield of 90percent. m.p.254~257°C; IR (KBr): 3334.61, 3095.36, 1770.03, 1751.21, 1619.29, 1533.45, 1470.52, 1336.55, 903.33, 852.46 cm-1; UV-VIS (CH3OH), λ/nm: 210, 321nm; 1H NMR (400 MHz, CDCl3): δ 10.74(s, 1H), 8.25(d, 1H), 7.97(s, 1H), 7.69(d, 1H); ESI-MS for C8H4N2O4 [M+H]+: calcd:193.13, found:193.08; Anal. Calcd for C8H4N2O4: C, 50.01; H, 2.10; N, 14.58. Found: C, 50.05; H, 2.06; N, 14.56.
87.6% at -4 - 20℃; for 0.666667 h; Weigh isatin5.00g (33.98mmol), potassium nitrate 3.44g (33.98mmol), in which case stirredslowly 15mL dissolved in 20mL, concentrated sulfuric acid, respectively, andthen at 0 ~ -4 , the isatin concentrated sulfuric acidsolution was slowly added dropwise a solution of potassium nitrate inconcentrated sulfuric acid, after the addition was complete stirring wascontinued for 30min, and then stirred at room temperature 10min, TLC thereaction was complete, the mixture was poured into ice-water, stirred for30min, suction filtered to give a yellow solid, dried under vacuum oven to givethe desired product 5-nitro-indole-dione 5.72g, yield 87.6percent.
83.4% at -5 - 0℃; -5 conditions,5.9 g of isatin (II) were weighed in batches dissolved in 26 mL of cold concentrated sulfuric acid,A mixture of 2 mL of fuming nitric acid and 3 mL of concentrated sulfuric acid was slowly added dropwise,And the reaction temperature was controlled around 0 ° C,After completion of the reaction, the reaction was continued for 3 hours.After completion of the reaction, the mixture was poured into a beaker containing 100 g of crushed ice,Filtration, ice water washing to neutral,The filter cake was dried to yield 6.4 g of the orange-red product (III) in 83.4percent yield,
65% at 60℃; for 1 h; The 5-nitroisatin (1) was prepared according to the reported literature refPreviewPlaceHolder[25]. Briefly, in a mixture of 50 g (35 mL, 0.50 mol) of conc. nitric acid and 74 g (40 mL, 0.75 mol) conc. sulfuric acid, isatin (48.50 g, 0.33 mol) was added slowly with frequent shaking in 500 mL round bottomed flask. Then the mixture was cooled by immersing the flask in crushed ice cold water. After adding all isatin, flask was fitted with reflux condenser and the mixture was heated on water bath maintaining the temperature at 60 °C for 1 h to obtain the desired compound 5-nitroisatin (1). Then the entire content was then transferred into a beaker containing 500 mL cold water, stirred in order to wash out as much acid from the desired product. When compound 1 settled completely to the bottom, the upper acid layer was removed from the mixture. Then the bottom layer was transferred to the separating funnel and shaked vigorously with about 50 mL of water. Then the residual layer was collected, dried with anhydrous calcium chloride and finally filtered to obtain the pure compound (1). Yield 65percent, Mp 230 °C; IR (KBr) cm-1: 3342 (NHstr), 2996 (ArCHstr), 1732 (CO, Isatin), 1570 (ArNO2, NO asym); 1348 (ArNO2, NO sym); 1H NMR (400 MHz, CDCl3, δ ppm): 7.02-7.94 (m, 3H, ArH), 8.92 (s, 1H, NH-Isatin); MS (EI) m/z 192 [M+]; Anal. Calcd for C8H4N2O4: C, 50.01; H, 2.10; N, 14.58. Found: C, 49.91; H, 2.12; N, 14.62.
62% at 60℃; Cooling with ice Compound indoline-2, 3-dione (48.5 g, 0.33 mol) was added into a mixture of 50 g (35 mL, 0.5 mol) of conc. nitric acid and 74 g (40 mL, 0.75 mol) conc. sulfuric acid with frequent shaking in 500-mL round bottomed flask, keeping the mixture cool by immersing the flask in ice cold water. After adding all indoline-2, 3-dione, flask was fitted with reflux condenser and the mixture was heated on water bath maintaining the temperature at 60 °C for 1 h to obtain the desired compound 5-nitroindoline-2, 3-dione (1). Content was then poured into a beaker containing 500 mL cold water, stirred in order to wash out as much acid from the desired compound. When compound (1) completely settled to the bottom, the upper acid liquor was completely poured off from the mixture. Then the residual liquid was transferred to the separating funnel and shaked vigorously with about 50 mL of water. Bottom layer was collected, dried with anhydrous calcium chloride and finally filtered to obtain the pure compound (1). Yield 62percent, mp 230 °C. IR (KBr) cm-1: 3306 (NHstr.), 3015 (Ar-CHstr.), 1725 (CO, Isatin), 1563 (NOstr.-sym.), 1325 (NOstr.-asym.), 1H NMR (CDCl3) δ (ppm): 7.12-7.89 (m, 3H, Ar-H), 9.53 (s, 1H, NH-Isatin); 13C NMR (DMSO-d6) δ (ppm): 107.34, 114.46, 127.24, 129.83, 144.24, 152.73, 160.26, 178.45.
47% at 0 - 20℃; for 2.5 h; The solution of isatin (52.09 g, 0.352 mol) in 520 mL of concentrated sulfuric acid was cooled down by ice bath to 0 0C. The potassium nitrate (35.55 g, 0.352 mol) was added portionwise over 2 hours maintaining the temperature between 0-5 0C. After complete addition the mixture was stirred at room temperature for 0.5 hour and poured into 1500 g of ice. The yellow precipitate was collected by vacuum filtration, washed with cold water and dried on air to give 32.16 g (47 percent yield) 5-nitro-isatin. mp (exp) = 243 0C (mp [5] = 251 0C). Spectrum NMR 1 (DMSO-d6, δ, ppm, J, Hz): 7.09 (d, 1H, J = 8.6); 8.2 (d, 1H, J = 2.3), 8.44 (dd,1H, J = 8.54, J = 2.5); 11.67 (s,1H).

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