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[ CAS No. 683-57-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Chemical Structure| 683-57-8

Chemical Structure| 683-57-8

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Quality Control of [ 683-57-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 683-57-8 ]

Product Citations

Product Citations

Design, synthesis and evaluation of thienopyridines as ligands of adenosine receptors

Nkomba, Gaofenngwe ; North-West University,2022.

More

Abstract: Despite the availability of various classes of antiepileptic drugs (AEDs), about one third of epileptic patients do not experience satisfactory seizure control with present treatments. This has been an important drive in the search for alternative epilepsy treatment. The endogenous nucleoside adenosine is a known anticonvulsant through activation of adenosine A1 receptors. The development of adenosine derivatives such as N6-cyclohexyladenosine (CHA) as anticonvulsants had limitations which include pronounced peripheral side effects, mainly cardiovascular effects. Over the years, non-nucleoside agonists have been investigated as an alternative set of compounds which are highly potent and selective to specific adenosine receptor (AR) subtypes. The aim of this study was to investigate the use of amino-3,5-dicyanopyridine and thieno[2,3- b]pyridine derivatives as potential A1 AR agonists. A total of 23 test compounds were synthesised (6a–s and 7a–d) and 7 of these were novel (6d and 6k–p), while 4 compounds (7a–d) have been synthesised before but have never been tested for AR affinity. The effect of intramolecular cyclisation that occurs during synthesis of thieno[2,3-b]pyridines from the intermediate compounds, amino-3,5-dicyanopyridines, in relation to AR binding was evaluated. Overall, amino-3,5-dicyanopyridine displayed superior activity towards rA1 ARs compared to thieno[2,3]pyridines. The general poor activity of thieno[2,3-b]pyridines suggest that the intramolecular cyclisation results in molecular stiffening or rigidity which negatively affects binding to the receptors, perhaps, due to steric hindrance. For instance, compound 6f (open ring) had a six-fold better inhibition constant (Ki) value of 48 nM for the A1 subtype compared to its closed ring counterpart compound 7d (rA1Ki = 305 nM). Generally, most amino-3,5- dicyanopyridines exhibited greater affinity toward the rA1 AR (Ki

Keywords: Epilepsy ; Antiepileptic drugs ; Adenosine A1/A2A receptor agonists ; Amino-3 ; 5- dicyanopyridine derivatives ; Thieno[2 ; 3-b]pyridine derivatives ; Intramolecular cyclisation

Purchased from AmBeed: 683-57-8 ; 68470-59-7 ; 123-11-5

Product Details of [ 683-57-8 ]

CAS No. :	683-57-8	MDL No. :	MFCD00008025
Formula :	C₂H₄BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JUIKUQOUMZUFQT-UHFFFAOYSA-N
M.W :	137.96	Pubchem ID :	69632
Synonyms :

Calculated chemistry of [ 683-57-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	22.51
TPSA :	43.09 ?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) :	-7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.58
Log Po/w (XLOGP3) :	-0.52
Log Po/w (WLOGP) :	-0.13
Log Po/w (MLOGP) :	-0.14
Log Po/w (SILICOS-IT) :	0.11
Consensus Log Po/w :	-0.02

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.3
Solubility :	68.9 mg/ml ; 0.499 mol/l
Class :	Very soluble
Log S (Ali) :	0.08
Solubility :	167.0 mg/ml ; 1.21 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.7
Solubility :	27.7 mg/ml ; 0.201 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 683-57-8 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P280-P301+P310-P305+P351+P338-P310	UN#:	2923
Hazard Statements:	H301-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 683-57-8 ]

* 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 [ 683-57-8 ]

[ 683-57-8 ] Synthesis Path-Downstream 1~4

1
[ 683-57-8 ]
[ 7768-28-7 ]
[ 176435-64-6 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1664 - 1675

2
[ 683-57-8 ]
[ 39987-25-2 ]
(4-methyloxycarbonylmethyl)piperazine-2,6-dione [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,2002,vol. 34,p. 87 - 94

3
[ 683-57-8 ]
[ 13589-72-5 ]
[ 1169561-46-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3732 - 3738

4
[ 683-57-8 ]
[ 403-01-0 ]
C₁₀H₁₀FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; for 1h;	[0710] 2-Bromoacetamide (0.46 g, 3.4 mmol) was added to methyl 3-fluoro-4- hydroxybenzoate (0.29 g, 1.7 mmol) and potassium carbonate (0.70 g, 5.0 mmol) in DMF (1 mL), and the mixture was heated to 65 °C for lh. The mixture was diluted with EA. and the organic phase was washed with water and brine, dried over anhydrous Na2S0 and concentrated. Compound 380-1 was crystallized from EA and collected by filtration (0.27 g, 71percent). NMR (400 MHz, dmso-i/6): delta 7.67-7.42 (m, 2H), 7.50 (br. s, 1H), 7.38 (br. s, 1H), 7.1 1 (t, J = 8.62, l H), 4.62 (s, 2H), 3.79 (s, 3H).

Reference： [1]Patent: WO2015/26792,2015,A1 .Location in patent: Paragraph 0710

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Isomers

Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

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[ 683-57-8 ]

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P234	Keep only in original container.
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Response
Code	Phrase
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P306	IF ON CLOTHING:
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P411
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P413
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P402 + P404	Store in a dry place. Store in a closed container.
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H240	Heating may cause an explosion
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H310	Fatal in contact with skin
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H316	Causes mild skin irritation
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Environmental hazards
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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