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Details

Stereochemistry ACHIRAL
Molecular Formula C24H20N4O
Molecular Weight 380.4418
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DMH-1

SMILES

CC(C)OC1=CC=C(C=C1)C2=CN3N=CC(=C3N=C2)C4=CC=NC5=C4C=CC=C5

InChI

InChIKey=JMIFGARJSWXZSH-UHFFFAOYSA-N
InChI=1S/C24H20N4O/c1-16(2)29-19-9-7-17(8-10-19)18-13-26-24-22(14-27-28(24)15-18)20-11-12-25-23-6-4-3-5-21(20)23/h3-16H,1-2H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24603907 | https://www.ncbi.nlm.nih.gov/pubmed/26683138 | https://www.ncbi.nlm.nih.gov/pubmed/26235139

DMH1 is a potent and selective inhibitor of BMP signaling. DMH1 is a direct inhibitor of ALK2 BMP type-I receptor ALK2 (activin receptor like kinase-2). DMH1 potently inhibits neoplastic phenotype in cancer cells.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 107.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vivo structure-activity relationship study of dorsomorphin analogues identifies selective VEGF and BMP inhibitors.
2010 Feb 19
Application of small organic molecules reveals cooperative TGFβ and BMP regulation of mesothelial cell behaviors.
2011 Sep 16
DMH1, a highly selective small molecule BMP inhibitor promotes neurogenesis of hiPSCs: comparison of PAX6 and SOX1 expression during neural induction.
2012 Jun 20
Bone morphogenetic protein-4 mediates cardiac hypertrophy, apoptosis, and fibrosis in experimentally pathological cardiac hypertrophy.
2013 Feb
DMH1 increases glucose metabolism through activating Akt in L6 rat skeletal muscle cells.
2014
(4-[6-(4-isopropoxyphenyl)pyrazolo [1,5-a]pyrimidin-3-yl] quinoline) is a novel inhibitor of autophagy.
2014 Nov
DMH1 (4-[6-(4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline) inhibits chemotherapeutic drug-induced autophagy.
2015 Jul
Inhibition of BMP signaling suppresses metastasis in mammary cancer.
2015 May 7
Bone morphogenetic protein signaling promotes tumorigenesis in a murine model of high-grade glioma.
2016 Jul
BMP Antagonist Gremlin 2 Limits Inflammation After Myocardial Infarction.
2016 Jul 22
Dorsomorphin homologue 1, a highly selective small-molecule bone morphogenetic protein inhibitor, suppresses medial artery calcification.
2017 Aug

Sample Use Guides

In Vivo Use Guide
Female mice expressing MMTV.PyVmT were implanted with a 6 week slow-release osmotic pump containing DMH1
Route of Administration: Unknown
In Vitro Use Guide
10-100 uM DMH1 dose-dependently inhibits astrocytic proliferation and migration in vitro
Name Type Language
DMH-1
Code English
4-[6-[4-(1-Methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
Systematic Name English
Quinoline, 4-[6-[4-(1-methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-
Systematic Name English
DMH 1
Code English
Code System Code Type Description
PUBCHEM
50997747
Created by admin on Sat Dec 16 20:01:22 GMT 2023 , Edited by admin on Sat Dec 16 20:01:22 GMT 2023
PRIMARY
FDA UNII
BVR5X3H6XM
Created by admin on Sat Dec 16 20:01:22 GMT 2023 , Edited by admin on Sat Dec 16 20:01:22 GMT 2023
PRIMARY
CAS
1206711-16-1
Created by admin on Sat Dec 16 20:01:22 GMT 2023 , Edited by admin on Sat Dec 16 20:01:22 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of DMH-1
NIH
NCATS
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