Category: 13534-97-9

In 2011,Joshi, Girdhar; Adimurthy, Subbarayappa published 《Environment-Friendly Bromination of Aromatic Heterocycles Using a Bromide-Bromate Couple in an Aqueous Medium》.Industrial & Engineering Chemistry Research published the findings.HPLC of Formula: 13534-97-9 The information in the text is summarized as follows:

Selective monobromination of aromatic heterocyclic compounds through in-situ acid activation of 2:1 bromide/bromate couple as a benign brominating reagent is described. The in-situ acid activation of a bromide-bromate couple generates the reactive species BrOH, and it is proved to be an efficient for the bromination of various heterocycles under mild aqueous conditions without the use of any catalyst. Heterocycles that had electron-rich substituents provided good yields. In the part of experimental materials, we found many familiar compounds, such as 6-Bromopyridin-3-amine(cas: 13534-97-9HPLC of Formula: 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.HPLC of Formula: 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2016,Schmidt, Sven Olaf; Naggert, Holger; Buchholz, Axel; Brandenburg, Hannah; Bannwarth, Alexander; Plass, Winfried; Tuczek, Felix published 《Thermal and Light-Induced Spin Transitions of FeII Complexes with 4- and 5-(Phenylazo)-2,2′-bipyridine Ligands: Intra- vs. Intermolecular Effects》.European Journal of Inorganic Chemistry published the findings.Product Details of 13534-97-9 The information in the text is summarized as follows:

Five new spin crossover complexes with 4- and 5-(phenylazo)-2,2-bipyridine (4-/5-PAbipy) ligands were synthesized and investigated with respect to their spin crossover (SCO) behavior. The results are compared to the thermal and light-induced spin transition properties of the parent SCO complexes [Fe(bpz)2(bipy)] (1) and [Fe(bipy)2(NCS)2] (2) (bpz = dihydro(bispyrazolyl)borate). [Fe(bpz)2(4-PAbipy)] (1a) undergoes a stepwise spin transition whereas [Fe(bpz)2(5-PAbipy)] (1b) exhibits a 1-step transition with a 6 K-wide hysteresis. For [Fe(bpz)2(tBu5-PAbipy)] (1c) the spin transition to the low-spin state is incomplete. Qual. similar changes of the SCO behavior are observed for [Fe(4-PAbipy)2(NCS)2] (2a) and [Fe(5-PAbipy)2(NCS)2] (2b). In comparison to the parent system 2, a strengthening of intermol. interactions leads to a stabilization of the low-spin state. Evidence for the LIESST behavior could be obtained for all new compounds by magnetic susceptibility measurements as well as UV/visible and resonance Raman spectroscopy. The results came from multiple reactions, including the reaction of 6-Bromopyridin-3-amine(cas: 13534-97-9Product Details of 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Product Details of 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Simmons, Bryan J.; Hoffmann, Marie; Champagne, Pier Alexandre; Picazo, Elias; Yamakawa, Katsuya; Morrill, Lucas A.; Houk, K. N.; Garg, Neil K. published 《Understanding and Interrupting the Fischer Azaindolization Reaction》.Journal of the American Chemical Society published the findings.Name: 6-Bromopyridin-3-amine The information in the text is summarized as follows:

Exptl. and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Addnl., an interrupted variant of Fischer azaindolization methodol. is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds. In the experiment, the researchers used 6-Bromopyridin-3-amine(cas: 13534-97-9Name: 6-Bromopyridin-3-amine)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Name: 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Spaulding, Andrew; Takrouri, Khuloud; Mahalingam, Pornachandran; Cleary, Dillon C.; Cooper, Harold D.; Zucchi, Paola; Tear, Westley; Koleva, Bilyana; Beuning, Penny J.; Hirsch, Elizabeth B.; Aggen, James B. published 《Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity》.Bioorganic & Medicinal Chemistry Letters published the findings.Application In Synthesis of 6-Bromopyridin-3-amine The information in the text is summarized as follows:

Previously the authors reported the results from an effort to improve Gram-neg. antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chem. campaign focused entirely on C-ring modifications. In that series the authors set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-neg. activity: (i) low MW (<400), (ii) high polarity (clogD7.4 <1), and (iii) zwitterionic character at pH 7.4. Indeed, the authors observed that only analogs residing within these limits were able to overcome these barriers. Herein the authors report the results from a parallel effort where the authors explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, anal. of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts. The experimental part of the paper was very detailed, including the reaction process of 6-Bromopyridin-3-amine(cas: 13534-97-9Application In Synthesis of 6-Bromopyridin-3-amine)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Application In Synthesis of 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Indian Journal of Heterocyclic Chemistry included an article by Bhasker, G. Vijaya; Satyanarayana, G. V.; Laxminarayana, E.; Latha, A.; Chary, M. Thirumala. Computed Properties of C5H5BrN2. The article was titled 《Synthesis, antibacterial activity, and docking studies of some new 2-substituted-1,8-naphthyridine derivatives》. The information in the text is summarized as follows:

Two series of novel 2-substituted-1,8-naphthyridine derivatives I (R = quinolin-3-yl, 4-AcC6H4, 2-Br-5-pyridyl, etc.) and II (R = quinolin-3-yl, 4-Cl-2-pyridyl, 2-BrC6H4) were synthesized. These compounds were evaluated for their antibacterial activity. Docking studies for these title compounds are also presented in this communication. In the part of experimental materials, we found many familiar compounds, such as 6-Bromopyridin-3-amine(cas: 13534-97-9Computed Properties of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Computed Properties of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2014,Guan, Aiying; Li, Huichao; Li, Zhinian; Yang, Fan; Xie, Yong; Yang, Xiaoping; Liu, Changling published 《N-Phenyl heteroarylamine analogues of fluazinam using the intermediate derivatization methods approach》.Journal of Chemical Sciences (Bangalore, India) published the findings.Recommanded Product: 6-Bromopyridin-3-amine The information in the text is summarized as follows:

Twenty-one N-Ph heteroarylamine analogs of fluazinam were prepared via nucleophilic substitution reaction of 2,6-dichloro-3,5-dinitrotoluene with heteroarylamines using the intermediate derivatization method. 2,6-Dichloro-3,5-dinitrotoluene, the key intermediate, was synthesized by nitration of 2,6-dichlorotoluene. Preliminary bioassays indicated that most of the compounds showed good fungicidal activity against rice blast. The activity of I was equal to that of fluazinam. The relationship between mol. structure and biol. activity suggested that introduction of electron-withdrawing groups in the pyridine ring was important for optimizing fungicidal activity against rice blast. The results came from multiple reactions, including the reaction of 6-Bromopyridin-3-amine(cas: 13534-97-9Recommanded Product: 6-Bromopyridin-3-amine)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Recommanded Product: 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,European Journal of Medicinal Chemistry included an article by Martin-Encinas, Endika; Rubiales, Gloria; Knudssen, Birgitta R.; Palacios, Francisco; Alonso, Concepcion. Synthetic Route of C5H5BrN2. The article was titled 《Straightforward synthesis and biological evaluation as topoisomerase I inhibitors and antiproliferative agents of hybrid chromeno[4,3-b][1,5]naphthyridines and chromeno[4,3-b][1,5]naphthyridin-6-ones》. The information in the text is summarized as follows:

Hybrid tetrahydrochromeno[4,3-b][1,5]naphthyridines I [R1 = H, F, Me; R2 = H, OMe; X = CH2], tetrahydrochromeno[4,3-b][1,5]naphthyridinones I [R1 = H, F; R2 = H, OMe, Br; X = C(O)], chromeno[4,3-b][1,5]naphthyridines II [X = CH2] and chromeno[4,3-b][1,5]naphthyridinones II [R3 = H, F, Me; R4 = H, OMe, Br; R5 = Ph, 4-MeOC6H4, 3,4-F2C6H3; Z = CH2, C(O)] were synthesized and evaluated as topoisomerase I inhibitors and antiproliferative agents. The synthetic route involved an intramol. Povarov [4 + 2]-cycloaddition of functionalized aldimines obtained by the condensation of 3-aminopyridine and aldehydes containing a double or triple carbon-carbon bond in ortho position and allowed the selective generation of three stereogenic centers. The subsequent dehydrogenation of the fused tetrahydrochromeno[4,3-b][1,5]naphthyridines I [X = CH2] and tetrahydrochromeno[4,3-b][1,5]naphthyridin-6-ones I [X = C=O] led to the formation of the corresponding tetracyclic chromeno[4,3-b][1,5]naphthyridine derivatives II [X = CH2] and chromeno[4,3-b][1,5]naphthyridin-6-ones II [X = C=O] in quant. yields. Some of the prepared products showed activity as inhibitors of topoisomerase I (TopI). Addnl., the cytotoxic behavior of these compounds was studied and the absence of cytotoxicity was observed against non-cancerous lung fibroblasts cell line (MRC5). Compound tetrahydrochromeno[4,3-b][1,5]naphthyridine I [R1 = R3 = H, R2 = Ph, X = CH2] showed excellent cytotoxic activity with a IC50 value of 1.03 ± 0.30 μM against the A549 cell line and a IC50 value of 1.75 ± 0.20 μM against the SKOV03 cell line. The obtained results point to these compounds as good antiproliferative candidates. Further, the physicochem. properties of these hybrid compounds were evaluated and could be considered as candidates for drugs with promising pharmacotherapeutic profiles similar to those of currently used drugs. In addition, docking experiments showed the possible mode of binding of these compounds and according to these studies the structural part corresponding to chromene or coumarin seems to play an important role in the interaction with the active site. The results came from multiple reactions, including the reaction of 6-Bromopyridin-3-amine(cas: 13534-97-9Synthetic Route of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Synthetic Route of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6-Bromopyridin-3-amineIn 2020 ,《Synthesis of novel hybrid quinolino[4,3-b][1,5]naphthyridines and quinolino[4,3-b][1,5]naphthyridin-6(5H)-one derivatives and biological evaluation as topoisomerase I inhibitors and antiproliferatives》 appeared in European Journal of Medicinal Chemistry. The author of the article were Martin-Encinas, Endika; Selas, Asier; Tesauro, Cinzia; Rubiales, Gloria; Knudsen, Birgitta R.; Palacios, Francisco; Alonso, Concepcion. The article conveys some information:

The topoisomerase I enzymic inhibition of hybrid quinolino [4,3-b][1,5]naphthyridines I [R1 = H, 9-OMe, 9-Br, 11-Br; R2 = H, tosyl; X = CH2, CO] and quinolino [4,3-b][1,5]naphthyridin-6(5H)-ones II [R3 = H, 9-OMe, 9-Br, 11-Br; X = CH2, CO] were investigated. First, the synthesis of these fused compounds was performed by intramol. [4 + 2]-cycloaddition reaction of functionalized aldimines obtained by the condensation of 3-aminopyridine and unsaturated aldehydes afforded corresponding hybrid 5-tosylhexahydroquinolino [4,3-b][1,5]naphthyridines I [R2 = tosyl; X = CH2] tetrahydroquinolino [4,3-b][1,5]naphthyridin-6(5H)-one compound I [R2 = tosyl; X = CO] with good to high yields. Subsequent dehydrogenation led to the corresponding more unsaturated dihydro [1,5]naphthyridine II [X = CH2] and [1,5]naphthyridin-6(5H)-one derivs II [X = CO] in quant. yields. Deprotection of tosyl group in compounds I [R1 = H, 9-Br; R2 = tosyl; X = CH2] with magnesium in acidic conditions led to hexahydroquinolino[4,3-b][1,5]naphthyridines derivatives I [R1 = H, 9-Br; R2 = H; X = CH2]. The new polycyclic products compounds I and II showed excellent-good activity as topoisomerase I (TopI) inhibitors that lead to TopI induced nicking of plasmids. This was consistent with the compounds acted as TopI poisons resulting in the accumulation of trapped cleavage complexes in the DNA. The cytotoxic effect on cell lines A549, SKOV3 and on non-cancerous MRC5 was also screened. Compound I [R1 = H; R2 = tosyl; X = CO] resulted the most cytotoxic compound with IC50 values of 3.25 ± 0.91μM and 2.08 ± 1.89μM against the A549 cell line and the SKOV3 cell line, resp. Also, compounds I [R1 = H; R2 = tosyl; X = CH2] and II [R3 = H] showed good cytotoxicity against these cell lines. None of the compounds presented cytotoxic effects against non-malignant pulmonary fibroblasts (MRC-5).6-Bromopyridin-3-amine(cas: 13534-97-9Reference of 6-Bromopyridin-3-amine) was used in this study.

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Reference of 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

SDS of cas: 13534-97-9In 2012 ,《Design, synthesis and structure-activity-relationship of 1,5-tetrahydronaphthyridines as CETP inhibitors》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Fernandez, Maria-Carmen; Escribano, Ana; Mateo, Ana I.; Parthasarathy, Saravanan; Martin de la Nava, Eva M.; Wang, Xiaodong; Cockerham, Sandra L.; Beyer, Thomas P.; Schmidt, Robert J.; Cao, Guoqing; Zhang, Youyan; Jones, Timothy M.; Borel, Anthony; Sweetana, Stephanie A.; Cannady, Ellen A.; Stephenson, Gregory; Frank, Scott; Mantlo, Nathan B.. The article contains the following contents:

This Letter describes the discovery and SAR optimization of 1,5-tetrahydronaphthyridines, a new class of potent CETP inhibitors. The effort led to the identification of I and II with in vitro human plasma CETP inhibitory activity in the nanomolar range (IC50 = 23 and 22 nM, resp.). Both I and II exhibited robust HDL-c increase in hCETP/hApoA1 dual heterozygous mice model. In addition to this study using 6-Bromopyridin-3-amine, there are many other studies that have used 6-Bromopyridin-3-amine(cas: 13534-97-9SDS of cas: 13534-97-9) was used in this study.

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.SDS of cas: 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Meena, Priyanka; Ayushee; Patel, Monika; Verma, Akhilesh K. published an article in Chemical Communications (Cambridge, United Kingdom). The title of the article was 《Transition-metal-free regioselective hydroamination of styrenes with amino-heteroarenes》.Safety of 6-Bromopyridin-3-amine The author mentioned the following in the article:

The base-mediated anti-Markovnikov hydroamination of functionally varied styrenes with amino-substituted pyridines, quinoline, pyrimidine, pyrazine with excellent regioselectivity to afford arylalkyl nitrogen heterocycles I [R1 = H, 4-Me, 6-Me, 4-CF3, etc; R2 = H, 4-Me, 4-Cl, etc.] and II [R3 = Ph, 4-MeC6H4, 1-naphthyl, 4-tBuC6H4; X = N; Y = N] was described. Double hydroamination was observed chemoselectively on the secondary amine, leaving the primary amine intact. The results came from multiple reactions, including the reaction of 6-Bromopyridin-3-amine(cas: 13534-97-9Safety of 6-Bromopyridin-3-amine)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Safety of 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem