Category: Triazoles

Exploring the effects of linker composition on site-specifically modified antibody-drug conjugates was written by Albers, Aaron E.;Garofalo, Albert W.;Drake, Penelope M.;Kudirka, Romas;de Hart, Gregory W.;Barfield, Robyn M.;Baker, Jeanne;Banas, Stefanie;Rabuka, David. And the article was included in European Journal of Medicinal Chemistry in 2014.Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) The following contents are mentioned in the article:

In the context of antibody-drug conjugates (ADCs), noncleavable linkers provide a means to deliver cytotoxic small mols. to cell targets while reducing systemic toxicity caused by nontargeted release of the free drug. Addnl., noncleavable linkers afford an opportunity to change the chem. properties of the small mol. to improve potency or diminish affinity for multidrug transporters, thereby improving efficacy. We employed the aldehyde tag coupled with the hydrazino-iso-Pictet-Spengler (HIPS) ligation to generate a panel of site-specifically conjugated ADCs that varied only in the noncleavable linker portion. The ADC panel comprised antibodies carrying a maytansine payload ligated through one of five different linkers. Both the linker-maytansine constructs alone and the resulting ADC panel were characterized in a variety of in vitro and in vivo assays measuring biophys. and functional properties. We observed that slight differences in linker design affected these parameters in disparate ways, and noted that efficacy could be improved by selecting for particular attributes. These studies serve as a starting point for the exploration of more potent noncleavable linker systems. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation was written by Goodman, C. Guy;Walker, Morgan M.;Johnson, Jeffrey S.. And the article was included in Journal of the American Chemical Society in 2015.Related Products of 1631733-83-9 The following contents are mentioned in the article:

A dynamic kinetic resolution of β-halo α-keto esters, RO₂CC(:O)CHXR’ [R = Me, Bu-t, R’ = CH₂Ph, X = Cl; R = Bu-t, R’ = Ph, Me, CH₂CH₂Me, CH₂CCSiMe₃, (CH₂)₃OCH₂Ph; R = Bu-t, R’ = Ph, X = F] in an asym. homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a³ → d³-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones I [R¹ = Ph, C₆H₄OMe-4, C₆H₄Cl-4, C₆H₄Me-4, C₆H₄Me-3, thien-2-yl, furan-2-yl, CH:CHPh-(E), CO₃Et] and II [R² = Ph, Me, CH₂CH:CH₂, CH₂CCSiMe₃, (CH₂)₃OCH₂Ph, X = Cl; R = Ph, X = F] with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodol. constitutes an intermol. DKR process to set three stereocenters during the key bond forming event. This study involved multiple reactions and reactants, such as (S)-5-Isopropyl-2-mesityl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1631733-83-9Related Products of 1631733-83-9).

(S)-5-Isopropyl-2-mesityl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1631733-83-9) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Related Products of 1631733-83-9

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

An efficient synthesis of 4-Thiocyanato anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H₂O was written by Dass, Reuben;Singleton, Justin D.;Peterson, Matt A.. And the article was included in Tetrahedron Letters in 2022.SDS of cas: 39876-84-1 The following contents are mentioned in the article:

Treatment of a variety of 2(3)-mono-substituted anilines with benzyltrimethylammonium dichloroiodate (1.2 equiv) and ammonium thiocyanate (1.2 equiv) in DMSO:H₂O (9:1) at 70°C gave the corresponding 4-thiocyanato-2(3)-substituted anilines ArSC≡N [Ar = 4-OH-3-MeC₆H₃, 4-NH₂-3-BrC₆H₃, 3-isoquinolyl, etc.] in excellent isolated yields (60-99%; ave. yield for all anilines = 90%). The reaction worked well for substrates with 2-halo, 2-alkoxy, 2-aryloxy, 2-alkyl, 2-dialkylamino, 2-N-sulfonylamino, 2-alkyn-1-yl, 2-cyano, 2-acyl, 2-sulfonyl, and 2-heteroaryl substitution. 3-Substituted, 3,5- or 2,6-disubstituted anilines and substituted phenols were also well tolerated. 4-Substituted anilines gave the corresponding 2-aminobenzothiazole products ArSC≡N, whereas 4-, 5-, 6-, or 7-substituted indoles were not reactive. Regioselective thiocyanation of 2-quinoline, 3-amino-1-methylpyrazole, 2-amino-4-phenylthiazole, and 2-phenylimidazo[1,2-a] pyridine was achieved in 93-99% yield, thus demonstrating the broad-substrate scope for this thiocyanation reaction. This study involved multiple reactions and reactants, such as 2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1SDS of cas: 39876-84-1).

2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. 1,2,3-Triazoles are usually prepared following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.SDS of cas: 39876-84-1

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reaction microarrays: a method for rapidly determining the enantiomeric excess of thousands of samples was written by Korbel, Gregory A.;Lalic, Gojko;Shair, Matthew D.. And the article was included in Journal of the American Chemical Society in 2001.Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) The following contents are mentioned in the article:

This contribution describes a new method that the authors have named reaction microarrays, in which DNA microarray technol. has been adapted to measure the ee of tens of thousands of samples rapidly and en masse. To evaluate the reaction microarray method, α-amino acids were used because of their fundamental chem. and biol. importance, the availability of structural diversity, and their bifunctional structure. Samples of N-Boc-protected α-amino acids were arrayed and covalently attached to amine-functionalized glass slides. Automated contact printing of nanoliter volumes from 2 mM solutions chemoselectively attached <10^-11 moles of amino acid to each spot on a glass slide in a spatially arrayed manner. Uncoupled surface amines were acetylated and en masse Boc-deprotection yielded the free amine. In analogy to DNA microarrays, where relative gene expression levels are measured by a ratio of fluorescent reporters, reaction microarrays utilize two fluorescent probes to measure a ratio of enantiomers. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

High-performance nanomaterials formed by rigid yet extensible cyclic β-peptide polymers was written by Fears, Kenan P.;Kolel-Veetil, Manoj K.;Barlow, Daniel E.;Bernstein, Noam;So, Christopher R.;Wahl, Kathryn J.;Li, Xianfeng;Kulp, III John L.;Latour, Robert A.;Clark, Thomas D.. And the article was included in Nature Communications in 2018.Reference of 156311-83-0 The following contents are mentioned in the article:

Organisms have evolved biomaterials with an extraordinary convergence of high mech. strength, toughness, and elasticity. In contrast, synthetic materials excel in stiffness or extensibility, and a combination of the two is necessary to exceed the performance of natural biomaterials. We bridge this materials property gap through the side-chain-to-side-chain polymerization of cyclic β-peptide rings. Due to their strong dipole moments, the rings self-assemble into rigid nanorods, stabilized by hydrogen bonds. Displayed amines serve as functionalization sites, or, if protonated, force the polymer to adopt an unfolded conformation. This mol. design enhances the processability and extensibility of the biopolymer. Mol. dynamics simulations predict stick-slip deformations dissipate energy at large strains, thereby, yielding toughness values greater than natural silks. Moreover, the synthesis route can be adapted to alter the dimensions and displayed chemistries of nanomaterials with mech. properties that rival nature. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Reference of 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. The triazole ring is a relatively stable functional group, and the triazole bond can be used for a variety of applications, such as replacing the phosphate backbone of DNA.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Reference of 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Lead identification and structure-activity relationships of heteroarylpyrazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists was written by Miah, Afjal H.;Copley, Royston C. B.;O’Flynn, Daniel;Percy, Jonathan M.;Procopiou, Panayiotis A.. And the article was included in Organic & Biomolecular Chemistry in 2014.Category: triazoles The following contents are mentioned in the article:

A knowledge-based library of aryl 2,3-dichlorophenylsulfonamides was synthesized and screened as human CCR4 antagonists, in order to identify a suitable hit for the start of a lead-optimization program. X-ray diffraction studies were used to identify the pyrazole ring as a moiety that could bring about intramol. hydrogen bonding with the sulfonamide NH and provide a clip or orthogonal conformation that was believed to be the preferred active conformation. Replacement of the core Ph ring with a pyridine, and replacement of the 2,3-dichlorobenzenesulfonamide with 5-chlorothiophenesulfonamide provided compound I which has excellent physicochem. properties and represents a good starting point for a lead optimization program. Electronic structure calculations indicated that the preference for the clip or orthogonal conformation found in the small mol. crystal structures of II and III was in agreement with the order of potency in the biol. assay. This study involved multiple reactions and reactants, such as 2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1Category: triazoles).

2-(1,2,4-Triazol-1-yl)aniline (cas: 39876-84-1) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Category: triazoles

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Automated Flow Synthesis of Peptide-PNA Conjugates was written by Li, Chengxi;Callahan, Alex J.;Phadke, Kruttika S.;Bellaire, Bryan;Farquhar, Charlotte E.;Zhang, Genwei;Schissel, Carly K.;Mijalis, Alexander J.;Hartrampf, Nina;Loas, Andrei;Verhoeven, David E.;Pentelute, Bradley L.. And the article was included in ACS Central Science in 2022.Synthetic Route of C17H27F6N7OP2 The following contents are mentioned in the article:

Antisense peptide nucleic acids (PNAs) have yet to translate to the clinic because of poor cellular uptake, limited solubility, and rapid elimination. Cell-penetrating peptides (CPPs) covalently attached to PNAs may facilitate clin. development by improving uptake into cells. We report an efficient technol. that utilizes a fully automated fast-flow instrument to manufacture CPP-conjugated PNAs (PPNAs) in a single shot. The machine is rapid, with each amide bond being formed in 10 s. Anti-IVS2-654 PPNA synthesized with this instrument presented threefold activity compared to transfected PNA in a splice-correction assay. We demonstrated the utility of this approach by chem. synthesizing eight anti-SARS-CoV-2 PPNAs in 1 day. A PPNA targeting the 5′ untranslated region of SARS-CoV-2 genomic RNA reduced the viral titer by over 95% in a live virus infection assay (IC₅₀ = 0.8 μM). Our technol. can deliver PPNA candidates to further investigate their potential as antiviral agents. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Synthetic Route of C17H27F6N7OP2).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Synthetic Route of C17H27F6N7OP2

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Use of onium salt-based coupling reagents in peptide synthesis was written by Albericio, Fernando;Bofill, Josep M.;El-Faham, Ayman;Kates, Steven A.. And the article was included in Journal of Organic Chemistry in 1998.Application of 156311-83-0 The following contents are mentioned in the article:

Peptide coupling methods derived from onium salts based on 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) are becoming incorporated in synthetic strategies more frequently than the classical carbodiimide methods. The authors have correlated the reactivity of various onium salts derived from HOXt (X = A, B), with the structure of the reagents in question. It was confirmed that the aza derivatives are more reactive than the parent benzotriazole derivatives in both activation and coupling. Also, the activation step is determined by the structure of the carbon skeleton, where pyrrolidino derivatives appear to be reagents of choice relative to the piperidino analogs or those derived from trialkylamines. Although phosphonium salts are slightly less reactive than the corresponding aminium/uronium salts, the former should be used for the activation of hindered species, since the latter may lead to the formation of guanidino derivatives This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Application of 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications.Triazole heterocyclic structures are found to form many weak nonbond interactions with the receptors and enzymes in biological systems.Application of 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts was written by Subiros-Funosas, Ramon;El-Faham, Ayman;Albericio, Fernando. And the article was included in Organic & Biomolecular Chemistry in 2010.Related Products of 156311-83-0 The following contents are mentioned in the article:

Recent studies described the great impact of a non-benzotriazolic family of coupling reagents based on Et 2-cyano-2-(hydroxyimino)acetate, Oxyma, as a powerful coupling methodol. for peptide synthesis. Here we present the synthesis and evaluation of the derived phosphonium salts O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and tetrafluoroborate (PyOxB). Both coupling reagents exhibited higher capacity to suppress racemization in various peptide models and enhanced solubility in DMF and DCM than benzotriazole-based reagents. In addition, the hexafluorophosphate analog PyOxP, combined excellent stability with outstanding efficiency in the assembly of demanding penta and decapeptides that include consecutive Aib residues. Cyclization models revealed the advantages of PyOxP, which rendered a higher percentage of cyclic material than other known potent phosphonium salts. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Related Products of 156311-83-0).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Related Products of 156311-83-0

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

An efficient PyAOP-based C⁴-amination method for direct access of oxidized 5-methyl-2′-deoxycytidine derivatives was written by Zheng, Xiu-An;Huang, Hua-Shan;Kong, Rui;Chen, Wei-Jie;Gong, Shan-Shan;Sun, Qi. And the article was included in Tetrahedron in 2018.Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) The following contents are mentioned in the article:

In the past decade, synthetic oxidized 5-methyl-2′-deoxycytidine nucleosides and their derivatives have become essential tools for epigenetic research. The low efficacy of both conventional and newly reported BOP methods on C⁴-amination of these specific oxidized ^5-MedU substrates urged us to systematically investigate how the nature of onium salt-based coupling reagents affects the C⁴-amination of pyrimidine nucleobases and lead us to the findings that different onium coupling reagents result in the formation of distinctive activation intermediates and PyAOP is much more potent than BOP in both activation and aminolysis steps. Direct amination without the need of ribose protection, ultrafast activation, tolerance to aqueous N-nucleophiles, and excellent yields for diverse oxidized ^5MedC derivatives are the advantages of this PyAOP-based C⁴-amination method. This study involved multiple reactions and reactants, such as ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)).

((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (cas: 156311-83-0) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities.Application In Synthesis of ((3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics