313735-62-5

Basic information

• Product Name: 4-Bromo-1-isopropyl-1H-pyrazole
• Synonyms: 4-BroMo-1-isopropylpyrazole;4-bromo-1-propan-2-ylpyrazole;4-BROMO-1-ISOPROPYL-1H-PYRAZOLE(WX637345)
• CAS NO: 313735-62-5
• Molecular Formula: C₆H₉BrN₂
• Molecular Weight: 189.05
• Product Categories: Azoles;blocks;Bromides
• Mol File: 313735-62-5.mol

Chemical Properties

• Boiling Point: 213.539 °C at 760 mmHg
• Flash Point: 82.946 °C
• Appearance: /
• Density: 1.492 g/cm³
• Refractive Index: 1.5070 to 1.5110
• Storage Temp.: 2-8°C
• PKA: 0.25±0.10(Predicted)
• CAS DataBase Reference: 4-Bromo-1-isopropyl-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1-isopropyl-1H-pyrazole(313735-62-5)
• EPA Substance Registry System: 4-Bromo-1-isopropyl-1H-pyrazole(313735-62-5)

Safety Data

• Hazardous Substances Data: 313735-62-5(Hazardous Substances Data)

Usage

General Description

4-Bromo-1-isopropyl-1H-pyrazole is a chemical compound with the molecular formula C6H9BrN2. It belongs to the class of organic compounds known as pyrazoles, which are characterized by a five-membered ring structure containing two nitrogen atoms and three carbon atoms. This particular compound contains a bromine atom and an isopropyl group attached to the pyrazole ring. It is primarily used as a building block in organic synthesis, particularly in the pharmaceutical industry where it can be incorporated into the structure of drug candidates. It is also used in research settings as a reagent in chemical reactions, and as a reference standard in analytical chemistry. The compound's properties and reactivity make it valuable for a range of applications in drug discovery and development, as well as in academic and industrial research.

Upstream product

• 2075-45-8 4-bromo-1H-pyrazole 
• 75-26-3 isopropyl bromide 
• 75-03-6 ethyl iodide 
• 75-30-9 2-iodo-propane 

Downstream Products

• 879487-10-2 1-isopropylpyrazole-4-boronic acid pinacol ester 
• 313735-67-0 1-(propan-2-yl)-1H-pyrazole-4-carbaldehyde 

Relevant articles and documents

PHD INHIBITOR COMPOUNDS, COMPOSITIONS, AND METHODS OF USE

The present invention provides, in part, novel small molecule inhibitors of PHD, having a structure according to Formula (I), and sub-formulas thereof: or a pharmaceutically acceptable salt thereof. The compounds provided herein can be useful for treatment of diseases including heart (e.g. ischemic heart disease, congestive heart failure, and valvular heart disease), lung (e.g., lung inflammation, pneumonia, acute lung injury, pulmonary hypertension, pulmonary fibrosis, and chronic obstructive pulmonary disease), respiratory (e.g., respiratory infection, acute respiratory distress syndrome), liver (e.g. acute liver failure and liver fibrosis and cirrhosis), and kidney (e.g. acute kidney injury and chronic kidney disease) disease, inflammatory bowel disease (IBD), ischemic reperfusion injury (e.g., stroke), and retinopathy of prematurity (ROP).

NURR1 RECEPTOR MODULATORS

Described herein, inter alia, are Nurr1 receptor modulators and uses thereof. In an aspect is provided a method for treating a disease associated with dysregulation and/or degeneration of dopaminergic neurons in the central nervous system of a subject in need thereof, the method including administering to the subject in need thereof a therapeutically effective amount of a compound described herein.

PYRAZOLE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to pyrazole compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the pyrazole compounds described herein in the potential treatment or prevention of neurological and psych

Identification of nicotinamide phosphoribosyltransferase (NAMPT) inhibitors with no evidence of CYP3A4 time-dependent inhibition and improved aqueous solubility

Herein we report the optimization efforts to ameliorate the potent CYP3A4 time-dependent inhibition (TDI) and low aqueous solubility exhibited by a previously identified lead compound from our NAMPT inhibitor program (1, GNE-617). Metabolite identification studies pinpointed the imidazopyridine moiety present in 1 as the likely source of the TDI signal, and replacement with other bicyclic systems was found to reduce or eliminate the TDI finding. A strategy of reducing the number of aromatic rings and/or lowering c Log D7.4 was then employed to significantly improve aqueous solubility. These efforts culminated in the discovery of 42, a compound with no evidence of TDI, improved aqueous solubility, and robust efficacy in tumor xenograft studies.

PROTEIN KINASE INHIBITORS

A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

Difluoromethyl ketones: Potent inhibitors of wild type and carbamate-insensitive G119S mutant Anopheles gambiae acetylcholinesterase

Malaria is a devastating disease in sub-Saharan Africa, and current vector control measures are threatened by emerging resistance mechanisms. With the goal of developing new, selective, resistance-breaking insecticides we explored α-fluorinated methyl ketones as reversible covalent inhibitors of Anopheles gambiae acetylcholinesterase (AgAChE). Trifluoromethyl ketones 5 demonstrated remarkable volatility in microtiter plate assays, but 5c,e-h exhibited potent (1-100 nM) inhibition of wild type (WT) AgAChE and weak inhibition of resistant mutant G119S mutant AgAChE. Fluoromethyl ketones 10c-i exhibited submicromolar to micromolar inhibition of WT AgAChE, but again only weakly inhibited G119S AgAChE. Interestingly, difluoromethyl ketone inhibitors 9c and 9g had single digit nanomolar inhibition of WT AgAChE, and 9g had excellent potency against G119S AgAChE. Approach to steady-state inhibition was quite slow, but after 23 h incubation an IC50 value of 25.1 ± 1.2 nM was measured. We attribute the slow, tight-binding G119S AgAChE inhibition of 9g to a balance of steric size and electrophilicity. However, toxicities of 5g, 9g, and 10g to adult A. gambiae in tarsal contact, fumigation, and injection assays were lower than expected based on WT AgAChE inhibition potency and volatility. Potential toxicity-limiting factors are discussed.

Fragment-based identification of amides derived from trans-2-(pyridin-3-yl) cyclopropanecarboxylic acid as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)

Potent, trans-2-(pyridin-3-yl)cyclopropanecarboxamide-containing inhibitors of the human nicotinamide phosphoribosyltransferase (NAMPT) enzyme were identified using fragment-based screening and structure-based design techniques. Multiple crystal structures were obtained of initial fragment leads, and this structural information was utilized to improve the biochemical and cell-based potency of the associated molecules. Many of the optimized compounds exhibited nanomolar antiproliferative activities against human tumor lines in in vitro cell culture experiments. In a key example, a fragment lead (13, KD = 51 μM) was elaborated into a potent NAMPT inhibitor (39, NAMPT IC 50 = 0.0051 μM, A2780 cell culture IC50 = 0.000 49 μM) which demonstrated encouraging in vivo efficacy in an HT-1080 mouse xenograft tumor model.

PROTEIN KINASE INHIBITORS

A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.

Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK)

Because of the critical roles of aberrant signaling in cancer, both c-MET and ALK receptor tyrosine kinases are attractive oncology targets for therapeutic intervention. The cocrystal structure of 3 (PHA-665752), bound to c-MET kinase domain, revealed a novel ATP site environment, which served as the target to guide parallel, multiattribute drug design. A novel 2-amino-5-aryl-3-benzyloxypyridine series was created to more effectively make the key interactions achieved with 3. In the novel series, the 2-aminopyridine core allowed a 3-benzyloxy group to reach into the same pocket as the 2,6-dichlorophenyl group of 3 via a more direct vector and thus with a better ligand efficiency (LE). Further optimization of the lead series generated the clinical candidate crizotinib (PF-02341066), which demonstrated potent in vitro and in vivo c-MET kinase and ALK inhibition, effective tumor growth inhibition, and good pharmaceutical properties.