Home Nitriles (βR)-β-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile

(βR)-β-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile

CAS No.:
941678-49-5
Catalog Number:
AG00350P
Molecular Formula:
C17H18N6
Molecular Weight:
306.3650
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)
In Stock USA
United States
$119
- +
10mg
98%(HPLC)
In Stock USA
United States
$136
- +
100mg
98%(HPLC)
In Stock USA
United States
$286
- +
250mg
98%(HPLC)
In Stock USA
United States
$453
- +
Product Description
Catalog Number:
AG00350P
Chemical Name:
(βR)-β-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile
CAS Number:
941678-49-5
Molecular Formula:
C17H18N6
Molecular Weight:
306.3650
MDL Number:
MFCD12031592
IUPAC Name:
(3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile
InChI:
InChI=1S/C17H18N6/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16/h6,8-12,15H,1-5H2,(H,19,20,21)/t15-/m1/s1
InChI Key:
HFNKQEVNSGCOJV-OAHLLOKOSA-N
SMILES:
N#CC[C@@H](n1ncc(c1)c1[nH]cnc2c1ccn2)C1CCCC1
UNII:
82S8X8XX8H
Properties
Complexity:
453  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
306.159g/mol
Formal Charge:
0
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
306.373g/mol
Monoisotopic Mass:
306.159g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
83.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.1  
Literature
Title Journal
Momelotinib versus best available therapy in patients with myelofibrosis previously treated with ruxolitinib (SIMPLIFY 2): a randomised, open-label, phase 3 trial. The Lancet. Haematology 20180201
Impairment of human neural crest cell migration by prolonged exposure to interferon-beta. Archives of toxicology 20170101
Differences in gene expression and alterations in cell cycle of acute myeloid leukemia cell lines after treatment with JAK inhibitors. European journal of pharmacology 20151015
White-to-brown metabolic conversion of human adipocytes by JAK inhibition. Nature cell biology 20150101
Structure-activity relationship of 3,5-diaryl-2-aminopyridine ALK2 inhibitors reveals unaltered binding affinity for fibrodysplasia ossificans progressiva causing mutants. Journal of medicinal chemistry 20141009
The novel Janus kinase inhibitor ruxolitinib confers protection against carbon tetrachloride-induced hepatotoxicity via multiple mechanisms. Chemico-biological interactions 20140905
Alopecia areata is driven by cytotoxic T lymphocytes and is reversed by JAK inhibition. Nature medicine 20140901
The evaluation of p,p'-DDT exposure on cell adhesion of hepatocellular carcinoma. Toxicology 20140801
Discovery and development of Janus kinase (JAK) inhibitors for inflammatory diseases. Journal of medicinal chemistry 20140626
Ruxolitinib and tofacitinib are potent and selective inhibitors of HIV-1 replication and virus reactivation in vitro. Antimicrobial agents and chemotherapy 20140401
JAK inhibitors: treatment efficacy and safety profile in patients with psoriasis. Journal of immunology research 20140101
Identification of potent Yes1 kinase inhibitors using a library screening approach. Bioorganic & medicinal chemistry letters 20130801
Myelofibrosis: an update on current pharmacotherapy and future directions. Expert opinion on pharmacotherapy 20130501
Regulation of inflammatory responses in tumor necrosis factor-activated and rheumatoid arthritis synovial macrophages by JAK inhibitors. Arthritis and rheumatism 20121201
Discovery of potent and selective pyrazolopyrimidine janus kinase 2 inhibitors. Journal of medicinal chemistry 20121126
Ruxolitinib: in the treatment of myelofibrosis. Drugs 20121112
Ruxolitinib, an oral JAK1 and JAK2 inhibitor, in myelofibrosis. Expert opinion on pharmacotherapy 20121101
Targeting JAK1/2 and mTOR in murine xenograft models of Ph-like acute lymphoblastic leukemia. Blood 20121025
Preliminary clinical activity of a topical JAK1/2 inhibitor in the treatment of psoriasis. Journal of the American Academy of Dermatology 20121001
Role of additional novel therapies in myeloproliferative neoplasms. Hematology/oncology clinics of North America 20121001
Current outlook on molecular pathogenesis and treatment of myeloproliferative neoplasms. Molecular diagnosis & therapy 20121001
Advances in the management of myelofibrosis. Cancer control : journal of the Moffitt Cancer Center 20121001
[Novel therapeutic options in the treatment of BCR/ABL-negative myeloproliferative neoplasms]. Deutsche medizinische Wochenschrift (1946) 20121001
Therapeutic effects of ruxolitinib in patients with myelofibrosis without clinically significant splenomegaly. Blood 20120927
Inhibition of JAKs in macrophages increases lipopolysaccharide-induced cytokine production by blocking IL-10-mediated feedback. Journal of immunology (Baltimore, Md. : 1950) 20120915
Ruxolitinib inhibits transforming JAK2 fusion proteins in vitro and induces complete cytogenetic remission in t(8;9)(p22;p24)/PCM1-JAK2-positive chronic eosinophilic leukemia. Blood 20120816
Long-term outcomes of 107 patients with myelofibrosis receiving JAK1/JAK2 inhibitor ruxolitinib: survival advantage in comparison to matched historical controls. Blood 20120809
How I treat polycythemia vera. Blood 20120712
Ruxolitinib for myelofibrosis therapy: current context, pros and cons. Leukemia 20120701
Identification of imidazo-pyrrolopyridines as novel and potent JAK1 inhibitors. Journal of medicinal chemistry 20120628
U.S. Food and Drug Administration approval: ruxolitinib for the treatment of patients with intermediate and high-risk myelofibrosis. Clinical cancer research : an official journal of the American Association for Cancer Research 20120615
The effect of CYP3A4 inhibition or induction on the pharmacokinetics and pharmacodynamics of orally administered ruxolitinib (INCB018424 phosphate) in healthy volunteers. Journal of clinical pharmacology 20120601
Ruxolitinib: the first FDA approved therapy for the treatment of myelofibrosis. Clinical cancer research : an official journal of the American Association for Cancer Research 20120601
Phase 2 study of the JAK kinase inhibitor ruxolitinib in patients with refractory leukemias, including postmyeloproliferative neoplasm acute myeloid leukemia. Blood 20120517
Ruxolitinib (Jakafi) for myelofibrosis. The Medical letter on drugs and therapeutics 20120402
Kinase domain mutations confer resistance to novel inhibitors targeting JAK2V617F in myeloproliferative neoplasms. Leukemia 20120401
Breakthroughs in myeloproliferative neoplasms. Hematology (Amsterdam, Netherlands) 20120401
JAK2 inhibitors and their impact in myeloproliferative neoplasms. Hematology (Amsterdam, Netherlands) 20120401
JAK inhibitors for myeloproliferative neoplasms: clarifying facts from myths. Blood 20120322
New generation small-molecule inhibitors in myeloproliferative neoplasms. Current opinion in hematology 20120301
Management of myeloproliferative neoplasms: from academic guidelines to clinical practice. Current hematologic malignancy reports 20120301
JAK inhibition with ruxolitinib versus best available therapy for myelofibrosis. The New England journal of medicine 20120301
A double-blind, placebo-controlled trial of ruxolitinib for myelofibrosis. The New England journal of medicine 20120301
Ruxolitinib. Nature reviews. Drug discovery 20120201
Ruxolitinib: the first agent approved for myelofibrosis. Clinical advances in hematology & oncology : H&O 20120201
Incyte comes of age with JAK inhibitor approval. Nature biotechnology 20120109
STAT3 is activated by JAK2 independent of key oncogenic driver mutations in non-small cell lung carcinoma. PloS one 20120101
Serious adverse events during ruxolitinib treatment discontinuation in patients with myelofibrosis. Mayo Clinic proceedings 20111201
Ruxolitinib for the treatment of myelofibrosis. Drugs of today (Barcelona, Spain : 1998) 20111101
Comprehensive analysis of kinase inhibitor selectivity. Nature biotechnology 20111030
Long-term outcome of treatment with ruxolitinib in myelofibrosis. The New England journal of medicine 20111013
Ruxolitinib: a new JAK1/2 inhibitor that offers promising options for treatment of myelofibrosis. Future oncology (London, England) 20110901
A potential role of ruxolitinib in leukemia. Expert opinion on investigational drugs 20110801
Targeting myeloproliferative neoplasms with JAK inhibitors. Current opinion in hematology 20110301
JAK inhibitor therapy for myelofibrosis: critical assessment of value and limitations. Leukemia 20110201
JAK inhibition in myelofibrosis. The New England journal of medicine 20101216
Diamino-1,2,4-triazole derivatives are selective inhibitors of TYK2 and JAK1 over JAK2 and JAK3. Bioorganic & medicinal chemistry letters 20101215
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry. Chemistry & biology 20101124
Metabolism, excretion, and pharmacokinetics of [14C]INCB018424, a selective Janus tyrosine kinase 1/2 inhibitor, in humans. Drug metabolism and disposition: the biological fate of chemicals 20101101
Ruxolitinib, a selective JAK1 and JAK2 inhibitor for the treatment of myeloproliferative neoplasms and psoriasis. IDrugs : the investigational drugs journal 20100601
Preclinical characterization of the selective JAK1/2 inhibitor INCB018424: therapeutic implications for the treatment of myeloproliferative neoplasms. Blood 20100415
Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction. Organic letters 20090507
Novel strategies for patients with chronic myeloproliferative disorders. Current opinion in hematology 20090301
Therapeutic potential of JAK2 inhibitors. Hematology. American Society of Hematology. Education Program 20090101
Properties