1670-87-7

Basic information

• Product Name: 1H-INDOLE-5-CARBOXAMIDE, 97%
• Synonyms: 1H-INDOLE-5-CARBOXAMIDE, 97%;SD-169;1H-Indole-5-carboxamide(9CI);5-(Aminocarbonyl)-1H-indole, 5-Carbamoylindole, 5-Carboxamidoindole;5-(AMinocarbonyl)-1H-indole;5-CarbaMoylindole;p38 MAP Kinase Inhibitor VII, SD-169
• CAS NO: 1670-87-7
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17262
• Product Categories: AMIDE;Heterocyclic Compounds
• Mol File: 1670-87-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 159-163 °C
• Boiling Point: 457.624 °C at 760 mmHg
• Flash Point: 230.563 °C
• Appearance: /
• Density: 1.328 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.717
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 16.25±0.30(Predicted)
• CAS DataBase Reference: 1H-INDOLE-5-CARBOXAMIDE, 97%(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE-5-CARBOXAMIDE, 97%(1670-87-7)
• EPA Substance Registry System: 1H-INDOLE-5-CARBOXAMIDE, 97%(1670-87-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 1670-87-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1670-87-7 differently. You can refer to the following data:
1. 1H-Indole-5-carboxamide (SD-169) is a p38α MAPK-selective inhibitor. 1H-Indole-5-carboxamide (SD-169) prevents the development and progression of diabetes in nonobese diabetic (NOD) mice by inhibiting T cell infiltration and activation.
2. SD 169 is a selective ATP competitive inhibitor of the MAP kinases p38α (IC50 = 3.2 nM) and p38β (IC50 = 122 nM). It has no inhibitory effect against a panel of other kinases, including p38γ MAP kinase, ERK2, JNK-1, and MAPKAPK-2, when tested in vitro at 50 μM. SD 169 is orally active, significantly reducing p38 MAP kinase expression in T cells of nonobese diabetic mice when delivered in chow at 600 mg/kg. In this model, SD 169 also reduced the incidence of diabetes, lowered blood glucose, and improved glucose homeostasis. SD 169 also enhances axonal regeneration after sciatic nerve crush injury in rats, when given by gavage (30 mg/kg) before and after nerve damage.
3. 1H-Indole-5-carboxamide (SD-169) is a p38α MAPK-selective inhibitor. 1H-Indole-5-carboxamide (SD-169) prevents the development and progression of diabetes in nonobese diabetic (NOD) mice by inhibiting T cell infiltration and activation.

Biological Activity

Selective, orally active, ATP-competitive inhibitor of p38 α MAPK (IC 50 values are 3.2, 122 and > 50000 nM for p38 α , p38 β and p38 γ respectively). Demonstrates no activity against a range of other kinases including ERK2, JNK1 and MAPKAP2. Prevents development of diabetes and alleviates mild and moderate hyperglycaemic states in NOD mice.

references

[1] medicherla s, protter a a, ma j y, et al. preventive and therapeutic potential of p38α-selective mitogen-activated protein kinase inhibitor in nonobese diabetic mice with type 1 diabetes[j]. journal of pharmacology and experimental therapeutics, 2006, 318(1): 99-107.[2] myers r r, sekiguchi y, kikuchi s, et al. inhibition of p38 map kinase activity enhances axonal regeneration[j]. experimental neurology, 2003, 184(2): 606-614.

InChI:InChI=1/C9H8N2O/c10-9(12)7-1-2-8-6(5-7)3-4-11-8/h1-5,11H,(H2,10,12)

Upstream product

• 1011-65-0 5-methoxycarbonylindole 
• 15861-24-2 1H-indole-5-carbonitrile 
• 10075-50-0 5-bromo-1H-indole 
• 15226-74-1 dicobalt octacarbonyl 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 18169-72-7 trimethylsilyl isocyanide 

Downstream Products

• 81881-74-5 5-aminomethylindole 
• 143612-79-7 3-(4-chlorobutyl)-5-cyanoindole 
• 276863-95-7 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile 
• 114948-09-3 5-Thiocarbamoyl-indol 
• 1215298-54-6 1-[4-(trifluoromethyl)benzoyl]-1H-indole-5-carboxamide 

Relevant articles and documents

BICYCLIC HETEROARYL DERIVATIVES AS ECTONUCLEOTIDE PYROPHOSPHATASE PHOSPHODIESTERASE 1 INHIBITORS

The present disclosure provides certain bicyclic heteroaryl compounds that inhibit ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) enzymatic activity and are therefore useful for the treatment of diseases and conditions modulated at least in part by ENPP1. In some embodiments, the bicyclic heteroaryl compounds includes those of Formula (I). Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions

Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.

Design and synthesis of novel 2-(indol-5-yl)thiazole derivatives as xanthine oxidase inhibitors

Xanthine oxidase (XO) inhibitors have been widely used for the treatment of gout. Indole rings are frequently used as active scaffold in designing inhibitors for enzymes. Herein, we describe the structure-activity relationship for novel xanthine oxidase inhibitors based on indole scaffold. A series of novel tri-substituted 2-(indol-5-yl)thiazole derivatives were synthesized, and their in vitro inhibitory activities against xanthine oxidase and in vivo efficacy lowering uric acid level in blood were measured. Among them, 2-(3-cyano-2-isopropylindol-5-yl)-4-methylthiazole-5-carboxylic acid exhibits the most potent XO inhibitory activity (IC50 value: 3.5 nM) and the excellent plasma uric acid lowering activity. Study of structure activity relationship indicated that hydrophobic moiety (e.g., isopropyl) at 1-position and electron withdrawing group (e.g., CN) at 3-position of indole ring and small hydrophobic group (CH3) at 4-position of the thiazole ring enhanced the XO inhibitory activity. Hydrophobic substitution such as isopropyl at 1-position of the indole moiety without any substitution at 2-position has an essential role for enhancing bioavailability and therefore for high in vivo efficacy.