1-(2,4-ジクロロフェニル)-5-(4-ヨードフェニル)-4-メチル-N-(ピペリジン-1-イル)-1H-ピラゾール-3-カルボキサミド

N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamide

HCID 2125CAS 183232-66-8

基本情報

標準SMILES: Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(I)cc1
InChIKey: BUZAJRPLUGXRAB-UHFFFAOYSA-N
分子式: C22H21Cl2IN4O
平均分子量: 555.2 g/mol
単同位体質量: 554.01371465

概要

AM-251 is a carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor. It has a role as an antidepressant, an antineoplastic agent, an apoptosis inducer and a CB1 receptor antagonist. It is a dichlorobenzene, a member of pyrazoles, a carbohydrazide, an organoiodine compound and an amidopiperidine.

名称と識別子

優先名称: N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamide
IUPAC: 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
現地名: 1-(2,4-ジクロロフェニル)-5-(4-ヨードフェニル)-4-メチル-N-(ピペリジン-1-イル)-1H-ピラゾール-3-カルボキサミド
英語名: AM 251
分子式: C22H21Cl2IN4O
分子量: 555.24

名称と別名

N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamideRefChem:556854AM251183232-66-8AM-251AM 2511-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide(S)-6-Hydroxy NicotineN-(Piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide1h-pyrazole-3-carboxamide, 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-n-1-piperidinyl-1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide

名称をさらに表示

1-(2,4-ジクロロフェニル)-5-(4-ヨードフェニル)-4-メチル-N-(ピペリジン-1-イル)-1H-ピラゾール-3-カルボキサミド1-(2,4-ジクロロフェニル)-N-ピペリジノ-4-メチル-5-フェニル-1H-ピラゾール-3-カルボアミド1-(2,4-ジクロロフェニル)-4-メチル-5-フェニル-N-(ピペリジン-1-イル)-1H-ピラゾール-3-カルボキサミドAM AMCS-985AM 251 NEWAM-251 ,99%WIZ degrader 9AM251, 10 mM in DMSOCB1 antagonist AM251

3I4FA44MAICHEMBL2859321-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidyl)pyrazole-3-carboxamideSMR000466284SR-01000597360UNII-3I4FA44MAIAM 251 (pharmaceutical)C22H21Cl2IN4O

データベース識別子

CAS: 183232-66-8
PubChem CID: 2125
DTXSID: DTXSID7042695
ChEMBL: CHEMBL285932
ChEBI: CHEBI:90724
UNII: 3I4FA44MAI
EC Number: 634-045-8
Nikkaji: J1.080.914B

物性

構造計算による物性

XLogP: 6.5
極性表面積: 50.2 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 4
重原子数: 30
形式電荷: 0
複雑度: 585

実験および物理化学的性質

LogP4.9

物理化学的性質

融点: 195 · 195-196℃
比重(密度): 1.65 · 1.65±0.1 g/cm3(Predicted)
貯蔵温度: Store at RT
溶解性: 10 mg/mL、可溶 · DMSO: >10 mg/mL、可溶
外見: 個体
酸解離定数(Pka): 11.31 · 11.31±0.20(Predicted)
色: 白い
安定性: -20 °C · -20°C の DMSO またはエタノール溶液で最大 3 か月間保存できます。
InChI: 1S/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
InChIKey: BUZAJRPLUGXRAB-UHFFFAOYSA-N
SMILES: Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCCCC4
CAS データベース: 183232 · 183232-66-8

化学的性質

化学的特性White to Off-White Solid

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (97.5%)

安全データ

wgk: 3
hs_code: 2933.39.6190
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
Hazard Classifications: Aquatic Chronic 4
ストレージクラス: 11 - Combustible Solids

化学と産業

応用分野 · 2 件

説明AM251 is a cannabinoid 1 (CB1) receptor 1 antagonist. It binds to CB1 receptors in rat forebrain membrane preparations (Ki = 7.5 nM) and is selective over CB2 receptors in mouse spleen preparations (Ki = 2,290 nM) in radioligand binding assays. AM251 inhibits GTPγS binding induced by the CB receptor agonist CP 55,940 in HEK293 cells expressing human CB1 receptors (EC50 = 8 nM). AM251 (10 mg/kg) decreases immobility time in the forced swim test in wild-type but not CB1 receptor-deficient mice. It reduces fasting-induced food intake and body weight gain in mice when administered at a dose of 30 mg/kg. AM251 also induces GTPγS binding in HEK293 cells expressing the orphan receptor GPR55 (EC50 = 39 nM) and potentiates GABA-induced GABAA receptor currents (EC50 = 0.4 μM). It prevents TGF-β1-induced epithelial-to-mesenchymal transition (EMT), inhibits SMAD2/3 and p38 MAPK activation, and reduces the expression of EMT-related transcription factors in HK-2 renal tubule epithelial cells. AM251 induces cell cycle arrest at the G2/M phase and apoptosis in A375 human melanoma cells.

使用Inhibitor of CB1 receptors. AM 251is a biarylpyrazole compound which has been considered for many years as the prototypical cannabinoid (CB) receptor antagonist

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