20615-76-3

Usage

General Description

Benzenemethanol, 2-azido- is a chemical compound with the molecular formula C7H7N3O. It is a derivative of benzyl alcohol, with an azide group attached to the carbon atom. Benzenemethanol, 2-azido- is known for its reactivity in azide-alkyne click chemistry, which is commonly used for bioconjugation and materials synthesis. It is often used as a precursor in the synthesis of various organic compounds and pharmaceuticals. However, it is important to handle Benzenemethanol, 2-azido- with caution, as the azide group can be explosive and toxic if mishandled. Therefore, proper safety protocols should be followed when working with benzenemethanol, 2-azido-.

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 31656-92-5 1-azido-2-methyl-benzene 
• 612-25-9 2-Nitrobenzyl alcohol 
• 552-89-6 2-nitro-benzaldehyde 
• 16714-25-3 2-azidobenzaldehyde 
• 87199-14-2 2-(hydroxymethyl)phenylboronic acid 
• 45754-05-0 o-Hydroxymethyl-benzoldiazonium 
• 118-92-3 anthranilic acid 

Downstream Products

• 71559-28-9 2-phenyl-1,4-dihydro-2H-2λ⁵-spiro[benzo[d][1,3,2]oxazaphosphinine-2,2'-[1,3,2]dioxaphospholane] 
• 16714-25-3 2-azidobenzaldehyde 
• 133390-63-3 2-<(Triphenylphosphoranylidene)amino>benzyl Alcohol 
• 159428-13-4 Bis(2,2'-diazidobenzyl) ether 
• 529-23-7 o-aminobenzaldehyde 
• 655230-45-8 (2-azido-5-bromophenyl)methanol 
• 389132-05-2 methanesulfonic acid 2-azidobenzylester 
• 120692-81-1 1-azido-2-(chloromethyl)benzene 
• 940938-72-7 C₁₀H₁₀ClN₃O 
• 940938-73-8 C₁₀H₉Cl₂N₃ 
• 940938-74-9 C₁₀H₈ClN₃O 
• 655229-97-3 dithiocarbonic acid O-ethyl ester S-(2-azido-5-bromobenzyl) ester 
• 566942-93-6 dithiocarbonic acid S-(5-bromo-2-diphenylvinylideneamino-benzyl) ester O-ethyl ester 
• 655230-14-1 dithiocarbonic acid O-ethyl ester S-(5-bromo-2-triphenylphosphoranylideneamino)benzyl ester 

Relevant academic research and scientific papers

Synthesis of 2,3,4-tri-substituted 3,4-dihydroquinazolines via tandem nucleophilic addition/epoxy ring-opening cyclization methodology using N-(2-Oxiranylphenyl)carbodiimides with nucleophiles

N-(2-Oxiranylphenyl)carbodiimides, which were synthesized via an aza-Wittig reaction of the corresponding functionalized iminophosphoranes with aromatic and aliphatic isocyanates, underwent O-, S-, C-, or N-nucleophilic addition onto a cumulene, followed by an epoxy ring-opening cyclization with the newly formed NH-nucleophile in a one-pot reaction to furnish 2,3-disubstituted 4-(hydroxymethyl)-3,4-dihydroquinazolines in a highly stereospecific manner. The Japan Institute of Heterocyclic Chemistry.

Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation

A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.

Leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry. Part II

Aminopeptidase N (APN) has been proved to be deeply associated with cancer angiogenesis, metastasis and invasion. Therefore, APN gains increasing attention as a promising anti-tumor target. In the current study, we report the design, synthesis, biological evaluation and structure-activity relationship of one new series of leucine ureido derivatives containing the 1,2,3-triazole moiety. Among them, compound 31f was identified as the best APN inhibitor with IC50 value being two orders of magnitude lower than that of the positive control bestatin. Compound 31f possessed selective cytotoxicity to several tumor cell lines over the normal cell line human umbilical vein endothelial cells (HUVECs). Notably, when combined with 5-fluorouracil (5-Fu), 31f exhibited synergistic anti-proliferation effect against several tumor cell lines. At the same concentration, 31f exhibited much better anti-angiogenesis activities than bestatin in the HUVECs capillary tube formation assay and the rat thoracic aorta rings test. In the in vitro anti-invasion assay, 31f also exhibited superior potency over bestatin. Moreover, considerable in vivo antitumor potencies of 31f alone or in combination with 5-Fu were observed without significant toxic signs in a mouse heptoma H22 tumor transplant model.

1. 2, 3 - Triazole class aminopeptidase N inhibitor and its preparation method and application (by machine translation)

The invention discloses a 1, 2, 3 - triazole class aminopeptidase N inhibitor and its preparation method and application. The invention relates to compounds having the general formula (I) or (II) the structure of the shown. The invention also provides the 1, 2, 3 - triazole class and in preparation method of preparation for preventing or treating the abnormal activity of aminopeptidase diseases associated with application of the medicament. (by machine translation)

Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan

Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a >10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.

Synthesis of Gallic-Acid-1-Phenyl-1H-[1,2,3]Triazol-4-yl Methyl Esters as Effective Antioxidants

Using a click chemistry approach, a series of gallic-acid-1-phenyl-1H-[1,2,3]triazol-4-ylmethyl esters was synthesized to develop more effective antioxidants. The results of DPPH screening indicate that few of the synthesized analogs display better antioxidant effect compared to the standards. Among all, compounds, 9 and 20 displayed highest DPPH radical scavenging effect with IC50 values as low as 6.4±0.2 and 7.9±0.4 μM respectively, compared to the standard ascorbic acid (IC50=12±0.8 μM) and gallic acid (IC50=9.0±0.6 μM). Compound 10 also displayed a potent antioxidant effect with IC50 of 10.80±0.4 μM. This study provides an important aspect with regard to the use of these gallic-acid based synthetic antioxidants in food industry as dietary supplements.

Intramolecular Amido Transfer Leading to Structurally Diverse Nitrogen-Containing Macrocycles

Reported herein is the development of rhodium-catalyzed intramolecular amido transfer as an efficient route to nitrogen-containing macrocycles starting from acetophenone ketoximes tethered with either aryl or alkyl azides. Facile generation of rhodacycles and metal imido intermediates was the key to success in this mechanistic scaffold to represent the first example of an intramolecular inner-sphere C?H amination. While substrates bearing aryl azides underwent a monomeric ring formation in high yields, a dimeric double cyclization took place exclusively with alkyl-azide-tethered ketoximes, thus affording up to 36-membered azamacrocyclic products.

Alkyne-azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors: Via the PI3K/Akt/NF-kB pathway

Herein, we report the isolation and synthetic modification of dehydrozingerone (DHZ, 1), a secondary metabolite present in the rhizome of Zingiber officinale. We synthesized O-propargylated dehydrozingerone, which was subsequently coupled by alkyne-azide cycloaddition (3-20) using click chemistry. The compounds (1-20) were evaluated for their in vitro cytotoxic activity in a panel of three cancer cell lines. Among all the DHZ derivatives, 3, 6, 7, 8, 9 and 15 displayed potent cytotoxic potential with an IC50 value ranging from 1.8-3.0 μM in MCF-7, PC-3 and HCT-116 cell lines. Furthermore, compound 7 has proven to be the most potent cytotoxic compound in all the three distinct cancer cell lines and also demonstrated significant anti-invasive potential in prostate cancer. The mechanistic study of compound 7 showed that it not only suppressed the AKT/mTOR signalling which regulates nuclear transcription factor-NF-kB but also augmented the expression of anti-invasive markers E-cadherin and TIMP. Compound 7 significantly decreased the expression of pro-invasive markers vimentin, MMP-2 and MMP-9, respectively. This study underscores an efficient synthetic approach employed to evaluate the structure-activity relationship of dehydrozingerone (1) in search of potential new anticancer agents.

Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation

A new series of α-santonin derived acetyl santonous acid 1,2,3-triazole derivatives were synthesised using Huisgen 1,3-dipolar cyclo-addition reaction (click chemistry approach) and evaluated for their in vitro inhibition activity on concanavalin A (ConA) induced T cell proliferation and lipopolysaccharide (LPS) induced B cell proliferation. Among the synthesised series, compounds 2-10 and 19 exhibited significant inhibition against ConA and LPS stimulated T-cell and B-cell proliferation in a dose dependent manner. More significantly compounds 4, 9-10 and 19 exhibited potent inhibition activity with remarkably lower cytotoxicity on the mitogen-induced T cell and B cell proliferation at 1 μM concentration. The compound 6 displayed potent immunosuppressive effects with ～89% against LPS induced B-cell and ～83% against ConA stimulated T-cell proliferation at 100 μM concentration without cytotoxicity. Compound 10 was more selective against B cell proliferation and exhibited 81% and 69% suppression at 100 and 1 μM concentration respectively. The present study led to the identification of several santonin analogs with reduced cytotoxicity and strong inhibition activity against the cell proliferation induced by the mitogens.

Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents

Rapid and efficient synthesis of a phenyl-1H-1,2,3-triazole library enabled cost-effective biological testing of a range of novel non-steroidal anti-inflammatory drugs with potential for improved drug efficacy and toxicity profiles. Anti-inflammatory acti