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N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide

CAS No.
329198-87-0
Chemical Name:
N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide
Synonyms
C-178;2-Furancarboxamide, N-3-dibenzofuranyl-5-nitro-;N-(3-Dibenzofuranyl)-5-nitro-2-furancarboxamide;N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide;MITA,inhibit,Inhibitor,STING,MPYS,C178,ERIS,C-178,C 178,Stimulator of Interferon Genes,TMEM173
CBNumber:
CB44635440
Molecular Formula:
C17H10N2O5
Molecular Weight:
322.27
MDL Number:
MOL File:
329198-87-0.mol
Last updated:2023-05-18 11:31:08

N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide Properties

Melting point >225°C (dec.)
Boiling point 448.3±35.0 °C(Predicted)
Density 1.506±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO (up to 25 mg/ml)
form solid
pka 11.35±0.43(Predicted)
color Orange
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338

N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML3098 C-178 ≥98% (HPLC) 329198-87-0 5MG $89 2024-03-01 Buy
Sigma-Aldrich SML3098 C-178 ≥98% (HPLC) 329198-87-0 25MG $359 2024-03-01 Buy
Cayman Chemical 25860 C-178 329198-87-0 10mg $61 2024-03-01 Buy
Cayman Chemical 25860 C-178 329198-87-0 50mg $230 2024-03-01 Buy
Cayman Chemical 25860 C-178 329198-87-0 5mg $32 2024-03-01 Buy
Product number Packaging Price Buy
SML3098 5MG $89 Buy
SML3098 25MG $359 Buy
25860 10mg $61 Buy
25860 50mg $230 Buy
25860 5mg $32 Buy

N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide Chemical Properties,Uses,Production

Description

C-178 is a covalent inhibitor of stimulator of interferon genes (STING). It binds to Cys91 on STING to block its palmitoylation and prevents recruitment and phosphorylation of TBK1 in HEK293T cells. C-178 (0.01-1.25 μM) selectively reduces STING-, but not RIG-I- or TBK1-, mediated IFN-β reporter activity in HEK293 cells. It also prevents increases in Ifnb1 expression in bone marrow-derived macrophages (BMDMs) induced by cyclic di-GMP , double-stranded DNA, and LPS when used at a concentration of 0.5 μM.

Uses

N-?(3-?Dibenzofuranyl)-?5-?nitro-2-?furancarboxamide is synthesized from Dibenzo[b,d]furan-3-amine (D418205), which is a building block used as a reactant in the preparation of dibenzofuryl(phosphonomethyl)alanines as endothelin converting enzyme inhibitors.

in vitro

C-178 targets the poorly characterized N-terminal portion of mmSTING that includes the transmembrane domains. Moreover, C-178 interferes with this process by inhibiting the palmitoylation of STING. C-178 does not appreciably affect STING responses in human cells.C-178 (0-1 μM; 1 hour) alone does not appreciably affect the gene expression profile of BMDMs. In addition, it inhibits the CMA-induced phosphorylation of TBK1.C-178 (1 μM; 1 hour) decreases cdG, dsDNA, CMA and LPS-induced Ifnb1 expression in mouse bone marrow-derived macrophages.C-178 (1 μM; 0.5-4 hours) inhibits the CMA-induced p-TBK1 and sting protein expression as a time-dependent manner in mouse embryonic fibroblasts.

References

1) Haag?et al.?(2018),?Targeting STING with covalent small-molecule inhibitors; Nature?559?269

N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide Preparation Products And Raw materials

Raw materials

Preparation Products

N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide Suppliers

Global( 40)Suppliers
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ATK CHEMICAL COMPANY LIMITED
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Shanghai Chaolan Chemical Technology Center QQ:65489617 15618227136 info@SuperLan-chem.com China 9737 58
N-(dibenzo[b,d]furan-3-yl)-5-nitrofuran-2-carboxamide C-178 N-(3-Dibenzofuranyl)-5-nitro-2-furancarboxamide 2-Furancarboxamide, N-3-dibenzofuranyl-5-nitro- MITA,inhibit,Inhibitor,STING,MPYS,C178,ERIS,C-178,C 178,Stimulator of Interferon Genes,TMEM173 329198-87-0