6323-87-1

Usage

InChI:InChI=1/C9H17N/c1-6-7-10(8(2)3)9(4)5/h1,8-9H,7H2,2-5H3

Upstream product

• 108-18-9 diisopropylamine 
• 106-96-7 propargyl bromide 
• 6165-76-0 propargyl p-toluenesulfonate 
• 75-09-2 dichloromethane 
• 75-20-7 calcium carbide 
• 14326-36-4 2-Brom-3-(N,N-diisopropylamino)propen 

Downstream Products

• 709665-40-7 N,N-diisopropyl-3-(4-methoxyphenyl)prop-2-yn-1-amine 
• 6323-69-9 diisopropyl-pent-2-ynyl-amine 
• 1399807-12-5 C₃₇H₅₈N₄O₇Si₂ 
• 1399807-18-1 C₃₉H₃₉FN₄O₇ 
• 1399807-16-9 C₃₉H₄₀N₄O₈ 
• 1399807-14-7 C₂₅H₃₂N₄O₆ 
• 1356648-21-9 N-allyl-N-isopropyl-2-methyl-4-phenylbut-3-yn-2-amine 

Relevant academic research and scientific papers

Discovery of highly potent renin inhibitors potentially interacting with the S3' subsite of renin

To exploit the S3′ subsite of renin active site for renin inhibitor design, 42 aliskiren derivatives with modified P2' portion were designed, synthesized and biologically evaluated. Some highly potent renin inhibitors (IC50 50 Combining double low line 0.9 nM) and 39 (IC50 Combining double low line 0.7 nM) were over 2.5-fold more potent than aliskiren (IC50 Combining double low line 2.3 nM). SAR analysis indicated that incorporation of polar hydrophilic moieties into the P2' portion of renin inhibitors generally enhanced the potency. Consistently with this, molecular modeling study revealed that the triazole part of 39 could provide additional interactions to the S3' subsite of renin active site. Moreover, in vivo evaluation in the double transgenic mouse hypertension model demonstrated that 39 produced greater reduction of the mean arterial blood pressure than ariskiren at the doses of 17.0 and 34.0 1/4mol/kg, respectively. Taken together, the S3' subsite of renin active site merits further consideration for renin inhibitor design.

Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum

Using 2,8-bis(trifluoromethyl)quinoline, the pharmacophore of mefloquine, as scaffold, eleven novel triazole-linked compounds have been synthesised by the application of CuAAC chemistry. The in vitro biological activity of the compounds on the Plasmodium falciparum chloroquine-sensitive strain NF54 was then determined. The compounds all showed IC50s in the lower μM range with (1R,3S,5R)-N-{[1-(2,8-bis(trifluoromethyl)quinoline-4-yl)-1H-1,2,3-triazol-4-yl]methyl}adamantan-2-amine (29) exhibiting the best activity of 1.00 μM.

PROCESS FOR PRODUCING AN AMINOPROPYNE OR ENAMINONE

There is provided a process for producing an aminopropyne or an enaminone comprising the step of reacting a metal acetylide, an amine and a carbonyl-containing compound in the presence of a transition metal catalyst. There is also provided a process for producing an aminopropyne comprising the step of reacting a metal acetylide, an amine and a halide-containing compound in the presence of a transition metal catalyst at a reaction temperature of 50°C to 150°C. There are also provided processes to further synthesize the aminopropyne produced to obtain a butyneamine, another aminopropyne or a triazol.

Synthesis of functional acetylene derivatives from calcium carbide

AHA Erlebnis: CaC2, used to produce acetylene until several decades ago, is re-emerging as a cheap, sustainable resource synthesized from coal and lignocellulosic biomass. We report efficient catalytic protocols for the synthesis of functional acetylene derivatives from CaC2 through aldehyde, alkyne, and amine (AAA) as well as alkyne, haloalkane, and amine (AHA) couplings, and in addition demonstrate its use in click and Sonogashira chemistry, showing that calcium carbide is a sustainable and cost-efficient carbon source.

Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and β-amyloid aggregation inhibitors

A series of novel triazole-containing berberine derivatives were synthesized via the azide-alkyne cycloaddition reaction. Their biological activity as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. Among t

Copper(I)-catalyzed substitution reactions of propargylic amines: Importance of C(sp)-C(sp3) bond cleavage in generation of iminium intermediates

Substitution reactions of propargylic amines proceed in the presence of copper(I) catalysts. Mechanistic studies showed that C(sp)?C(sp3) bond cleavage assisted by nitrogen lone-pair electrons is essential for the reaction, and the resulting iminium intermediates undergo amine exchange, aldehyde exchange, and alkyne addition reactions. Because iminium intermediates are key to aldehyde?alkyne?amine (A3) coupling reactions, this transformation is effective not only for reconstruction of propargylic amines but also for chiral induction of racemic compounds in the presence of chiral catalysts.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS TYROSINE KINASE INHIBITORS

This invention provides compounds of formula (1) wherein X is C3-7 cycloalkyl, pyridinyl, pyrimidinyl or phenyl ring optionally substituted as described in claim 1, R1, R3 and R4 are chosen from the groups listed in claim 1. R2 is chosen from various unsaturated acyl groups listed in claim 1, with certain compounds being disclaimed. Use as tyrosine kinase inhibitors for the treatment of cancer and certain kidney diseases such as polycystic kidney disease.

6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity

A series of new 6-substituted-4-(3-bromophenylamino)quinazoline derivatives that may function as irreversible inhibitors of epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases have been prepared. These inhibitors have, at the C-6 position, butynamide, crotonamide, and methacrylamide Michael acceptors bearing water-solublilizing substituents. These compounds were prepared by acylation of 6-amino-4-(3-bromophenylamino)quinazoline with unsaturated acid chlorides or mixed anhydrides. We show that attaching a basic functional group onto the Michael acceptor results in greater reactivity, due to intramolecular catalysis of the Michael addition and/or an inductive effect of the protonated basic group. This, along with improved water solubility, results in compounds with enhanced biological properties. We present molecular modeling and experimental evidence that these inhibitors interact covalently with the target enzymes. One compound, 16a, was shown to have excellent oral activity in a human epidermoid carcinoma (A431) xenograft model in nude mice.

Substituted quinazoline derivatives

This invention provides compounds of formula 1 having the structure wherein: X, R1, R2, R3, R4, Z, X, and n are as defined hereinbefore in the specification, which are useful as antineoplastic agents and in the treatment of certain kidney diseases, such as polycystic kidney disease.

Studies of Tertiary Amine Oxides Part 10. Silylated Acetylenic Amines and the Corresponding N-Oxides

Ten silylated acetylenic amines were synthesized and converted into the corresponding tertiary N-oxides by oxidation with m-chloroperbenzoic acid.All compounds were fully characterised by elemental and spectral analyses.The carbon-13 spectra of the silylated acetylenic amines and the N-oxides were analysed and the N-oxidation effect was calculated.