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[ CAS No. 39603-24-2 ] {[proInfo.proName]}

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Chemical Structure| 39603-24-2
Chemical Structure| 39603-24-2
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Product Citations

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 [ 39603-24-2 ]

CAS No. :39603-24-2 MDL No. :MFCD00047219
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :(CH3)2C8H3NO2 InChI Key :HFZSCCJTJGWTDZ-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :38296
Synonyms :

Calculated chemistry of [ 39603-24-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.09
TPSA : 46.17 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.18
Solubility : 1.15 mg/ml ; 0.00659 mol/l
Class : Soluble
Log S (Ali) : -2.03
Solubility : 1.65 mg/ml ; 0.00943 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0495 mg/ml ; 0.000282 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 39603-24-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39603-24-2 ]

* 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 [ 39603-24-2 ]
  • Downstream synthetic route of [ 39603-24-2 ]

[ 39603-24-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 7343-12-6 ]
  • [ 39603-24-2 ]
YieldReaction ConditionsOperation in experiment
66% With sulfuric acid In water at 50 - 90℃; for 0.5 h; General procedure: To a flask (100 mL) which contained concentrated sulfuricacid (20 mL) was added N-2-(hydroxyimino)acetamidederivatives (7.0 g) in portions at 50 °C with vigorous stirring.The reaction temperature was maintained at 50 °C-75 °Cduring the addition. After the addition was completed, themixture was heated to 80 °C and stirred for 30 min. The reactionmixture was cooled to room temperature and thenpoured onto ice (250 g). The solid which resulted was filteredout and dried over air to yield the crude which waspurified by dissolving in dilute sodium hydroxide (5percent, 100mL) followed by acidified with 4N hydrochloric acid (20mL). The solid which formed was filtered out and dried overair to provide the purified compounds 15a-g.
Reference: [1] Journal of Chemical Research, Miniprint, 1998, # 7, p. 1425 - 1434
[2] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[4] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[5] Gazzetta Chimica Italiana, 1955, vol. 85, p. 840,841
[6] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1955, vol. &lt;8&gt;18, p. 647,653
[7] Chemische Berichte, 1992, vol. 125, # 4, p. 849 - 856
[8] Chemistry - A European Journal, 2008, vol. 14, # 36, p. 11565 - 11572
  • 2
  • [ 1421739-75-4 ]
  • [ 39603-24-2 ]
YieldReaction ConditionsOperation in experiment
60% at 80℃; for 0.666667 h; Cooling with ice General procedure: A round-bottom flask is charged with concentrated sulfuric acid (33 ml) and is magnetically stirred at 50 °C open to the atmosphere. To the acid was added 2-[(benzyloxy)imino]-N-(4-n-hexylphenyl) (11 g, 32.5 mmole) in portions over 30 minutes. On completion of the addition the mixture was heated at 80 °C for an additional 10 minutes then allowed to cool to room temperature. The dark viscous solution was subsequently added in portions with rapid stirring to ice (750 ml). The crude product was isolated by vacuum filtration, and the filter cake washed with water. The crude product was dried under vacuum to give 6.3 g (85 percent) of an orange solid.#10;#10;
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 8, p. 1008 - 1011
  • 3
  • [ 4102-54-9 ]
  • [ 39603-24-2 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 3, p. 998 - 1003
  • 4
  • [ 95-68-1 ]
  • [ 39603-24-2 ]
Reference: [1] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
  • 5
  • [ 79-37-8 ]
  • [ 95-68-1 ]
  • [ 39603-24-2 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 646
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 647
  • 6
  • [ 861586-96-1 ]
  • [ 64-17-5 ]
  • [ 39603-24-2 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 3182[2] Chemische Berichte, 1925, vol. 58, p. 686
  • 7
  • [ 64-17-5 ]
  • [ 39603-24-2 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1918, vol. 166, p. 953[2] Annales de Chimie (Cachan, France), 1919, vol. &lt;9&gt; 11, p. 115
  • 8
  • [ 64-19-7 ]
  • [ 39603-24-2 ]
  • [ 65-85-0 ]
Reference: [1] Chemische Berichte, 1923, vol. 56, p. 2117
  • 9
  • [ 39603-24-2 ]
  • [ 14438-32-5 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 583
[2] Journal of the American Chemical Society, 1965, vol. 87, # 24, p. 5554 - 5558
[3] Chemische Berichte, 1992, vol. 125, # 4, p. 849 - 856
[4] Chemistry - A European Journal, 2008, vol. 14, # 36, p. 11565 - 11572
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Acyl Group Substitution • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Alkylation of Enolate Ions • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amines Convert Acyl Chlorides into Amides • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Diorganocuprates Convert Acyl Chlorides into Ketones • Dithioacetal Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reaction • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hofmann Rearrangement • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Michael Addition • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Strecker Synthesis • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Wittig Reaction • Wolff-Kishner Reduction
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