[ CAS No. 91-56-5 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 91-56-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 91-56-5 ]

SDS Specification

Alternatived Products of [ 91-56-5 ]

Product Citations Expand+

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 , et al. J. Med. Chem.,2023,66(5):3372-3392. DOI: 10.1021/acs.jmedchem.2c01858 PubMed ID: 36825758

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

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 ...More

Product Details of [ 91-56-5 ]

CAS No. :	91-56-5	MDL No. :	MFCD00005718
Formula :	C₈H₅NO₂	Boiling Point :	-
Linear Structure Formula :	C₆H₄NH(CO)₂	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 ?2

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 1~4

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

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

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

Reference： [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 ]

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

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

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

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.

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.

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Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? 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 ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 91-56-5 ]

Amides

[ 39603-24-2 ]

5,7-Dimethylindoline-2,3-dione

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7-Methylindoline-2,3-dione

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[ 91-56-5 ]

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Ghs Precautionary Statements

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P102	Keep out of reach of children.
P103	Read label before use
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Code	Phrase
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P242	Use only non-sparking tools.
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P270	Do not eat, drink or smoke when using this product.
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P281	Use personal protective equipment as required.
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Code	Phrase
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 91-56-5 ] {[proInfo.proName]}

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