2468-55-5

Usage

Uses

Used in Organic Synthesis:
5-IODO-1-PENTYNE is used as a reagent in organic synthesis for the preparation of various organic compounds. Its unique reactivity allows it to participate in a range of chemical reactions, making it a versatile component in the creation of new molecules and materials.
Used in Chemical Research:
In the field of chemical research, 5-IODO-1-PENTYNE serves as a valuable tool for studying the properties and reactions of haloalkynes. Its presence in experiments can provide insights into the behavior of molecules containing both halogen and triple bond functionalities.
Used in Pharmaceutical Development:
5-IODO-1-PENTYNE is utilized in pharmaceutical development as a building block for the synthesis of potential drug candidates. Its unique chemical properties can contribute to the discovery of new therapeutic agents with novel mechanisms of action.
Used in the Production of Specialty Materials:
Due to its reactivity and structural features, 5-IODO-1-PENTYNE can be employed in the production of specialty materials, such as polymers and coatings, that exhibit specific properties desirable in various industries.
Safety Precautions:
Given its potentially hazardous nature, it is crucial to observe proper handling and safety precautions when working with 5-IODO-1-PENTYNE. This includes using appropriate personal protective equipment, working in well-ventilated areas, and following established safety protocols to minimize risks associated with its use.

Upstream product

• 14267-92-6 1-chloro-4-pentyne 
• 5390-04-5 pent-1-yn-5-ol 
• 68275-03-6 pent-4-yn-1-yl methanesulfonate 
• 77758-50-0 4-pentynyl-1-tosylate 

Downstream Products

• 15288-96-7 1-Phenyl-2-butyl-heptin-⁽⁶⁾-on-⁽¹⁾ 
• 68524-96-9 (2S,5R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-2-pent-4-ynyl-cyclohexanone 
• 67448-64-0 pent-4-yne-1-sulfonyl chloride 
• 64275-43-0 1,6-undecadiyne 
• 146445-27-4 4-methoxycarbonyl-non-3-en-8-ynoate de methyle 
• 5661-06-3 2,3-dihydro-1H-cyclopenta[b]quinoline 
• 83025-77-8 4-(4-pentynyl)-2-cyclohexenone 
• 127038-66-8 3-ethoxy-6-(4-pentynyl)-2-cyclohexenone 
• 88854-26-6 2-Pent-4-ynyl-cyclohexanol 
• 83025-76-7 5-isopropyl-4-(4-pentynyl)-2-cyclohexenone 
• 88904-92-1 6-(4-pentynyl)-5-isopropyl-3-ethoxy-2-cyclohexenone 
• 124419-09-6 C₂₀H₂₀O₂S₂ 
• 144463-52-5 methyl 2-(1-phenylsulfonylpyrrol-3-yl)hept-6-ynoate 
• 133931-62-1 C₂₀H₂₀O₃S 

Relevant academic research and scientific papers

Sulfonamido carboranes as highly selective inhibitors of cancer-specific carbonic anhydrase IX

Carbonic anhydrase IX (CA IX) is a transmembrane enzyme overexpressed in hypoxic tumors, where it plays an important role in tumor progression. Specific CA IX inhibitors potentially could serve as anti-cancer drugs. We designed a series of sulfonamide inhibitors containing carborane clusters based on prior structural knowledge of carborane binding into the enzyme active site. Two types of carborane clusters, 12-vertex dicarba-closo-dodecaborane and 11-vertex 7,8-dicarba-nido-undecaborate (dicarbollide), were connected to a sulfonamide moiety via aliphatic linkers of varying lengths (1–4 carbon atoms; n = 1–4). In vitro testing of CA inhibitory potencies revealed that the optimal linker length for selective inhibition of CA IX was n = 3. A 1-sulfamidopropyl-1,2-dicarba-closo-dodecaborane (3) emerged as the strongest CA IX inhibitor from this series, with a Ki value of 0.5 nM and roughly 1230-fold selectivity towards CA IX over CA II. X-ray studies of 3 yielded structural insights into their binding modes within the CA IX active site. Compound 3 exhibited moderate cytotoxicity against cancer cell lines and primary cell lines in 2D cultures. Cytotoxicity towards multicellular spheroids was also observed. Moreover, 3 significantly lowered the amount of CA IX on the cell surface both in 2D cultures and spheroids and facilitated penetration of doxorubicin. Although 3 had only a moderate effect on tumor size in mice, we observed favorable ADME properties and pharmacokinetics in mice, and preferential presence in brain over serum.

Synthesis and antiviral evaluation of nucleoside analogues bearing one pyrimidine moiety and two d-ribofuranosyl residues

A series of 1,2,3-triazolyl nucleoside analogues in which 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via polymethylene linkers to both nitrogen atoms of the heterocycle moiety (uracil, 6-methyluracil, thymine, quinazoline-2,4-dione, alloxazine) or to the C-5 and N-3 atoms of the 6-methyluracil moiety was synthesized. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. Antiviral assays revealed three compounds, 2i, 5i, 11c, which showed moderate activity against influenza virus A H1N1 with IC50 values of 57.5 μM, 24.3 μM, and 29.2 μM, respectively. In the first two nucleoside analogues, 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via butylene linkers to N-1 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine, respectively). In nucleoside analogue 11c, two 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached via propylene linkers to the C-5 and N-3 atoms of the 6-methyluracil moiety. Almost all synthesized 1,2,3-triazolyl nucleoside analogues showed no antiviral activity against the coxsackie B3 virus. Two exceptions are 1,2,3-triazolyl nucleoside analogs 2f and 5f, in which 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached to the C-5 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine respectively). These compounds exhibited high antiviral potency against the coxsackie B3 virus with IC50 values of 12.4 and 11.3 μM, respectively, although both were inactive against influenza virus A H1N1. According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 2i, 5i, and 11c against the H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRp). As to the antiviral activity of nucleoside analogs 2f and 5f against coxsackievirus B3, it can be explained by their interaction with the coat proteins VP1 and VP2.

Development and Application of a Chemical Probe Based on a Neuroprotective Flavonoid Hybrid for Target Identification Using Activity-Based Protein Profiling

Alzheimer's disease (AD) is the most common form of dementia, and up to now, there are no disease-modifying drugs available. Natural product hybrids based on the flavonoid taxifolin and phenolic acids have shown a promising pleiotropic neuroprotective profile in cell culture assays and even disease-modifying effects in vivo. However, the detailed mechanisms of action remain unclear. To elucidate the distinct intracellular targets of 7-O-esters of taxifolin, we present in this work the development and application of a chemical probe, 7-O-cinnamoyltaxifolin-alkyne, for target identification using activity-based protein profiling. 7-O-Cinnamoyltaxifolin-alkyne remained neuroprotective in all cell culture assays. Western blot analysis showed a comparable influence on the same intracellular pathways as that of the lead compound 7-O-cinnamoyltaxifolin, thereby confirming its suitability as a probe for target identification experiments. Affinity pulldown and MS analysis revealed adenine nucleotide translocase 1 (ANT-1) and sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) as intracellular interaction partners of 7-O-cinnamoyltaxifolin-alkyne and thus of 7-O-esters of taxifolin.

Protecting-Group-Free Total Synthesis of Chatenaytrienin-2

An efficient seven-step, protecting-group-free first total synthesis of chatenaytrienin-2 based on ring-closing metathesis and C(sp)-C(sp3) Sonogashira coupling with a 36.5% overall yield has been described. The ready availability of starting m

Synthesis of novel 1,2,3-triazolyl nucleoside analogues bearing uracil, 6-methyluracil, 3,6-dimethyluracil, thymine, and quinazoline-2,4-dione moieties

A series of novel 1,2,3-triazolyl nucleoside analogues was synthesized via the CuAAC reaction of N1-alkynyl uracil, 6-methyluracil, 3,6-dimethyl uracil, thymine and quinazolin-2,4-dione with protected azido β-D-ribofuranose. The obtained compounds differ in both the nature of the pyrimidine-2,4-dione fragment and the length of the polymethylene linker connecting it with the β-D-ribofuranosyl-1,2,3-triazol-4-yl moiety. The 1,2,3-triazolyl nucleoside analogues were evaluated for their cytotoxicity in vitro.

Photoinduced, Copper-Promoted Regio- and Stereoselective Decarboxylative Alkylation of α,β-Unsaturated Acids with Alkyl Iodides

The first example of UV light-induced, copper-catalyzed regio- and stereoselective decarboxylative coupling of α,β-unsaturated acids with alkyl iodides was reported. Under standard conditions, the 1°, 2°, and 3° alkyl iodides proceeded smoothly with the E-selective alkenes obtained in uniformly good yields and high stereoselectivities.

Lewis Acid-Catalyzed Intramolecular [3+2] Cross-Cycloaddition of Aziridine 2,2-Diesters with Conjugated Dienes for Construction of Aza-[n.2.1] Skeletons

A novel Lewis acid-catalyzed [3+2] intramolecular cross-cycloaddition (IMCC) between aziridine 2,2-diesters and conjugated dienes has been developed. This is the first regiospecific IMCC of intramolecular 1,3-dipolar cycloadditions of azomethine ylides with carbon=carbon double bonds, and supplies a general and efficient strategy for construction of structurally complex and diverse aza-[n.2.1] skeletons. The [3+2]IMCC could be carried out under mild conditions and in gram scale. More importantly, 3-alkyl-substituted aziridines were also successful. The excellent structural diversity, the facile operation and the versatile post-modifications will support the applications of the [3+2]IMCC in natural products synthesis and drugs discovery.

Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding

A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes

Approaches to polyunsaturated sphingolipids: New conformationally restrained analogs with minimal structural modifications

Conformationally restrained sphingolipids 1-4, arising from the introduction of a polyene or a polyenyne moiety as part of the sphingoid backbone, have been synthesized. While addition of polyene acetylides 6 and 7 to Garner's aldehyde afforded the corres

Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5-Hetero-Functionalized Triazoles

The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions with complete regioselectivity. It also features a broad substrate scope and good functional group compatibility.