6089-09-4

Usage

Uses

4-Pentynoic acid is used as a hypoglycemic agent for its ability to increase liver tyrosine aminotransferase and plasma corticosterone while decreasing blood sugar in rats.
Used in Pharmaceutical Industry:
4-Pentynoic acid is used as a building block for the synthesis of a library of eight sequence-defined model oligomers, which are essential in the development of novel pharmaceutical compounds.
Used in Chemical Synthesis:
4-Pentynoic acid is used as a key component in the one-pot synthesis of complex polycyclic heterocycles, such as benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives, which have potential applications in various fields, including pharmaceuticals and materials science.
Used in Organic Chemistry:
4-Pentynoic acid is utilized in the synthesis of various allenenols lactones, such as [5(E)-(2-allenylidene)-tetrahydro-2-furanones], which are valuable intermediates in organic chemistry and can be used to create a wide range of chemical compounds.
Used in Cancer Research:
4-Pentynoic acid is employed in the synthesis of a cytotoxic macrolide through ring-closing metathesis of a bis acetylene, which has potential applications in cancer research and the development of novel anticancer drugs.

InChI:InChI=1/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)/p-1

Synthetic route

pent-1-yn-5-ol (5390-04-5) → 4-pentynoic acid (6089-09-4)

Conditions	Yield
With Jones reagent In acetone at 20℃; for 1h;	99%
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%

Upstream product

• 98198-39-1 prop-2-yn-1-ylpropanedioic acid 
• 5390-04-5 pent-1-yn-5-ol 
• 106-96-7 propargyl bromide 
• 105-53-3 diethyl malonate 
• 627-15-6 1,3-dibromopropene 
• 63093-41-4 ethyl 4-pentynoate 
• 15719-64-9 methylammonium carbonate 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 78181-02-9 4,5-dibromopentanoic acid 
• 21565-82-2 methyl pent-4-ynoate 
• 18498-59-4 4-pentyn-1-al 
• 1431618-30-2 2-oxohex-5-ynal 
• 24342-04-9 methyl pent-2-ynoate 
• 128545-15-3 5-trimethylsilyl-pent-5-yn-1-oic acid 

Downstream Products

• 21565-82-2 methyl pent-4-ynoate 
• 91909-52-3 7-cyclohex-1-enyl-hepta-4,6-diynoic acid 
• 591-12-8 5-methyl-2-furanone 
• 21651-12-7 (E)-2,4-pentadienoic acid 
• 10008-73-8 5-methylenedihydrofuran-2-one 
• 1487-57-6 4,5-Dihydro-5-methoxy-5-methylfuran-2(3H)-one 
• 134031-01-9 (Z)-4-(phenylselenomethylene)butan-4-olide 
• 100780-23-2 (E)-4-(phenylselenomethylene)butan-4-olide 
• 16900-59-7 4-decynoic acid 
• 126378-11-8 4-pentynoic acid benzyl ester 
• 103437-70-3 5(E)-(3-phenylprop-2-ynylidene)tetrahydro-2-furanone 
• 109574-00-7 (E)-4-(phenylthiomethylene)butan-4-olide 
• 109574-01-8 (E)-4-Chloro-5-phenylsulfanyl-pent-4-enoic acid 
• 109574-02-9 (E)-5-Chloro-4-phenylsulfanyl-pent-4-enoic acid 

Relevant academic research and scientific papers

Development of a chemical probe for identifying protein targets of α-oxoaldehydes

The development of a chemical probe for identifying the protein targets of reactive electrophilic α-oxoaldehydes such as methylglyoxal is presented. The probe is evaluated against methylglyoxal using human serum albumin as well as using living cells and lysates.

Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity

Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.

DDX3X inhibitors, an effective way to overcome HIV-1 resistance targeting host proteins

The huge resources that had gone into Human Immunodeficiency virus (HIV) research led to the development of potent antivirals able to suppress viral load in the majority of treated patients, thus dramatically increasing the life expectancy of people living with HIV. However, life-long treatments could result in the emergence of drug-resistant viruses that can progressively reduce the number of therapeutic options, facilitating the progression of the disease. In this scenario, we previously demonstrated that inhibitors of the human DDX3X helicase can represent an innovative approach for the simultaneous treatment of HIV and other viral infections such as Hepatitis c virus (HCV). We reported herein 6b, a novel DDX3X inhibitor that thanks to its distinct target of action is effective against HIV-1 strains resistant to currently approved drugs. Its improved in vitro ADME properties allowed us to perform preliminary in vivo studies in mice, which highlighted optimal biocompatibility and an improved bioavailability. These results represent a significant advancement in the development of DDX3X inhibitors as a novel class of broad spectrum and safe anti-HIV-1 drugs.

Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid

The C16-C22 fragment with the acetylene terminus was constructed through the asymmetric dihydroxylation of the corresponding olefin, while the 15-iodo-olefin corresponding to the C11-C15 part was prepared via the asymmetric transfer hydrogenation of the corresponding acetylene ketone followed by hydrozirconation/iodination. Both pieces were joined by a Sonogashira coupling, and the product was further converted into the title compound via a Wittig reaction with the remaining C1-C10 segment and Boland reduction using Zn with TMSCl.

HETEROCYCLIC COMPOUNDS AND USE THEREOF

Heterocyclic compounds of Formula (I) shown herein. Also disclosed is a pharmaceutical composition containing one of the heterocyclic compounds. Further disclosed are methods of using one of the heterocyclic compounds for mobilizing hematopoietic stem cells and endothelial progenitor cells into the peripheral circulation, and for treating tissue injury, cancer, inflammatory disease, and autoimmune disease.

An Efficient Aerobic Oxidation Protocol of Aldehydes to Carboxylic Acids in Water Catalyzed by an Inorganic-Ligand-Supported Copper Catalyst

A method for the aerobic oxidation of aldehydes to carboxylic acids in water by using an inorganic-ligand-supported copper catalyst was developed. This method was performed with the use of atmospheric oxygen as the sole oxidant under extremely mild aqueous conditions, and furthermore, a wide range of aldehydes with various functional groups were tolerated. The copper catalyst could be recycled and used in successive reactions at least six times without any appreciable degradation in performance. This method is operationally simple and avoids the use of high-costing, toxic, air/moisture-sensitive, and commercially unavailable organic ligands. The generality of this method gives it potential to be used on the industrial scale.

Method for preparing acid through oxidating alcohols or aldehydes by oxygen

The invention provides a method for preparing acid through oxidating alcohols or aldehydes by using oxygen or oxygen in air as an oxidant. The method comprises the steps: oxidating the alcohols or aldehydes to produce the acid at room temperature in an organic solvent in a manner of taking ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidyl nitrogen oxide (TEMPO) and an inorganic halide as catalysts and taking the oxygen or air as an oxidant, and oxidating diols to produce lactone; or, carrying out a reaction on the aldehydes, which serve as a raw material, under neutral conditions by taking ferric nitrate as a catalyst, and oxidating the aldehydes to produce the acid and peroxy acid. The method has the advantages that the method is environmentally friendly, the cost is low, the yield is high, the atomic economical efficiency is high, the compatibility of substrate functional groups is good, the reaction conditions are mild, a reaction scale can be enlarged, and the like, so that the method is suitable for being applied to industrial production.

USE OF DDX3 INHIBITORS AS ANTIPROLIFERATIVE AGENTS

The present invention refers to compounds of formula I or II endowed with DDX3 inhibitory activity, relative pharmaceutical compositions and their use as antihyperproliferative agents. (I) or (II)

Traceless and Chemoselective Amine Bioconjugation via Phthalimidine Formation in Native Protein Modification

ortho-Phthalaldehyde (OPA) and its derivatives are found to react chemoselectively with amino groups on peptides and proteins rapidly and tracelessly under the physiological condition via formation of phthalimidines, which provides a novel and promising approach when performing bioconjugation on native proteins. The notable advantages of this method over the existing native protein lysine-labeling approaches include a traceless process, a self-reacting, specific and fast reaction, ease of operation, and the ability to use nonhydrolyzable reagents. Its applications have been effectively demonstrated including conjugation of peptides and proteins, and generation of an active PEGlyated l-asparaginase.

HUMAN HELICASE DDX3 INHIBITORS AS THERAPEUTIC AGENTS

The present invention refers to compounds endowed with RNA helicase DDX3 inhibitory activity of formula I and II and their therapeutic use, in particular for the treatment of viral diseases.