Category: 26187-28-0

Ueno, Tasuku published the artcileMechanism-Based Molecular Design of Highly Selective Fluorescence Probes for Nitrative Stress, Computed Properties of 26187-28-0, the publication is Journal of the American Chemical Society (2006), 128(33), 10640-10641, database is CAplus and MEDLINE.

Nitrative stress is implicated in various pathogenic processes, including neurodegenerative disorders, but there is no practical fluorescence probe which can monitor the generation of nitrative stress with high selectivity. To design a suitable fluorescence probe, the authors have first focused on the fluorescence quenching mechanism of the nitro group, which has been believed to be a unique quencher of fluorescent dyes. The authors found that nitro group-based fluorescence quenching could be explained in terms of an electron transfer process, from the excited fluorophore to the electron-deficient aromatic nitro moiety. By utilizing this result, the authors succeeded in developing novel fluorogenic probes, NiSPYs, which can selectively monitor the generation of nitrative stress based on aromatic nitration. NiSPYs showed strong fluorescence enhancement upon the reaction with nitrating agents, including peroxynitrite, but showed little or no fluorescence augmentation in the presence of other reactive oxygen species. NiSPYs should be potentially useful as tools to study the role of nitrative stress in various biol. applications.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C11H14O2, Computed Properties of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Franke, Jenna M. published the artcileBODIPY Fluorophores for Membrane Potential Imaging, Safety of 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, the publication is Journal of the American Chemical Society (2019), 141(32), 12824-12831, database is CAplus and MEDLINE.

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biol. compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chem. transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based, voltage-sensitive fluorophores (VF). The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two addnl. BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water-soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Safety of 2,4-Dimethyl-1H-pyrrole-3-carbonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Fischer, H. published the artcilePyrrolenitriles and some of their transformations, Related Products of nitriles-buliding-blocks, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1930), 2249-57, database is CAplus.

2,4-Dimethyl-3-cyano-5-carbethoxypyrrole, MeC:C(CN).CMe:CR.NH (I, R = CO₂Et) is saponified to the 5-CO₂H acid (II) (I, R =CO₂H) without the CN group being hydrolyzed, and distillation in vacuo gives 2,4-dimethyl-3-cyanopyrrole (III). The CN group is materially stabilized by its position on the nucleus, whereas when it is on a side chain, as in 2,4-dimethyl-3-Ω-cyano-Ω-carbetboxy-vinyl-5-carbethoxypyrrole, it can be hydrolyzed with extraordinary ease, the β-position being attacked first and then the α-position. III can be obtained still more easily by the Knorr pyrrole synthesis from AcCH₂CO₂Et and AcCH₂CONH₂, and AcCH₂NH₂.HCl instead of AcCH₂CO₂Et-NaNO₂ gives an even better yield. With HCHO and a little HCl III readily yields 3,3′,5,5′-tetramethyl-4,4′-dicyanopyrrometliane (IV) which, surprisingly enough, cannot be converted with either FeCl₃ or Br into the corresponding methene (V) although the V.HBr is obtained in good yield, with elimination of CO₂, from II with HCO₂H and 48% HBr on the H₂O bath. NH₄OH readily gives the free V in red needles which form metal complexes. III and HCN readily give an aldehyde (VI) (1, R = CHO), whose oxime yields with AC₂O 2,4-dimethyl-3,5-dicyanopyrrole (VII). With boiling HCl VI yields V.HCl. The CHO group in VI is reduced to Me by the Wolff-Kishner method, giving 2,4,5-trimethyl-3-eyanopyrrole, together with some 2,4,5-trimethylpyrrole. From VI and 2,3,4-trimethylpyrrole, cryptopyrrole and crypto-pyrrolecarboxylic acid were obtained 3,3′,4,5,5′-pentamethyl- (VII), 3,3′,5,5′-tetramethyl-4-ethyl- (VIII) and 3,3′,5,5′-ietramethyl-4-propionic acid-4′-cyanopyrromethene-HBr (IX), resp.; VIII was also obtained from cryptopyrrolealdehyde with III. These cyanomethenes were synthesized with the object of preparing porphyrins with CN groups on the nucleus but numerous attempts to do this failed. Porphyrin formation took place but only etioporphyrin II could be isolated. This negative result is perhaps due to the unreactiveness of the α-Me groups. Bromination of the 3 methenes could not be effected either and I (R = CO₂Et) is likewise unreactive toward Br, although with Br and NaBrO₃ 3 Br atoms can be introduced into the α-Me group, with simultaneous oxidation of the α-Me group, the product being 2-tribromomethyl-3-cyano-4-hydroxymethyl-5-carbethoxypyrrole (X). III can also be brominated on the nucleus in the α-position. With SO₂Cl₂ I gave a yellow oil yielding with H₂O 2-hydroxymethyl-3-cyano-4-methyl-5-carbethoxypyrrole (XI). With higher concentrations, 6 atoms Cl are introduced: the product is probably 2,4-bistrichloromethyl-3-cyano-5-carbethoxypyrrole (XII). II (about 40 g. from 60 g. I with boiling aqueous NaOH), m. 250°; 8 g. in vacuo at 150° gives 4 g. III, m. 107°. 2,4-Dimethyl-3-carboxamide-5-carbethoxypyrrole (1.8 g. from 12 g. AcCH₂-CO₂Et, NaNO₂, AcCH₂CONH₂ and Zn dust), m. 173°; 0.5 g. gives with boiling NaOAc-Ac₂O 0.3 g. I, which is obtained in 1 g. yield from 1.5 g. ACCH₂NH₂.HCl and AcCH-CONH₂ in NaOH. V.HBr (13-5 g. from 20 g. II), golden yellow, in. 242° (decomposition). V.HCl (1 g. from 2 g. II), m. 225° (decomposition). Free V, ruby-red, m. 280°(decomposition); Cu complex, C₃0H₂6N₈C₁1 crystals with metallic green surface luster, soluble in most solvents with red color; Co complex, green; On complex, 2C₃0H₂6N₈Zn.Zn(OAc)₂, pink, contains 2 active H atoms (Chugaev-Zerevitinov). XI, reddens and sinters 145-°, m. around 195-6°. XII (2.8 g. from 5 g. I, 20 g. SO₂Cl₂ and 20 cc. Et₂O), m. around 98°. X (about 20%), m. 183°, easily soluble in dilute alkalies, the yellow solution becoming dark brown and finally black (in 20% NaOH it at once darkens and decomposes), regenerates I on long boiling with Zn dust in AcOH. 2,4-Dimethyl-3-cyano-5-formylpyrrole (VI) (9-10 g. from 15 g. III in CHCl₃-Et₂O with anhydrous HCN), m. 223° oxime, m. 206°; semicarbazone, turns yellow 250° and gradually darkens and sinters; phenylhydrazone, m. 175°. VII, m. 209°. 2,4-Dimethyl-3-cya-no-5-bromopyrrole (0-5 g. from 0.4 g. III with Br-AcOH), darkens 130° and sinters without melting. VII (1.3g. from 0.75g. VI), yellow, decomposes 230°. VIII (80%), orange-red, darkens 190°, m. 241° IX, golden yellow, m. 240° (decomposition).

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wentrup, Curt published the artcile3-pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides and ring contraction to cyanopyrroles and cyanoindoles, Synthetic Route of 26187-28-0, the publication is Beilstein Journal of Organic Chemistry (2013), 743-753, database is CAplus and MEDLINE.

Precursors of 3-pyridylnitrene and 2- and 4-pyrimidinylcarbenes all afford mixtures of 2- and 3-cyanopyrroles on flash vacuum thermolysis, but 3-cyanopyrroles are the first-formed products. 3-Quinolylnitrenes and 4-quinazolinylcarbenes similarly afford 3-cyanoindoles. 2-Pyrimidinylcarbenes rearrange to 3-pyridylnitrenes, but 4-pyrimidinylcarbenes and 4-quinazolinylcarbenes do not necessarily rearrange to the corresponding 3-pyridylnitrenes or 3-quinolylnitrenes. The ring contraction reactions are interpreted in terms of ring opening of either the nitrenes or the diazacycloheptatetraenes to nitrile ylides.

Beilstein Journal of Organic Chemistry published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C2H2N4O2, Synthetic Route of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Genokhova, N. S. published the artcileSynthesis of metallic complexes of 1,19-dimethyloctadehydrocorrins with electron acceptor β-substituents, SDS of cas: 26187-28-0, the publication is Zhurnal Obshchei Khimii (1977), 47(1), 121-9, database is CAplus.

I (M = Co, Ni, R = Me, CH2CO2H, R’ = CH2CH2CO2H; R = CO2Et, CN, R’ = Me) were prepared by the oxidative cyclization of hexamethylbiline derivatives in the presence of Ni and Co ions. The hexamethylbiline derivatives were also prepared The complexes and the ligands were characterized by electronic and NMR spectra.

Zhurnal Obshchei Khimii published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, SDS of cas: 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ieda, Naoya published the artcileDevelopment of photoredox-reaction-driven NO-releasing reagents and application for photomanipulation of vasodilation, Application In Synthesis of 26187-28-0, the publication is Yuki Gosei Kagaku Kyokaishi (2020), 78(11), 1048-1057, database is CAplus.

Nitric oxide (NO) is a signaling mol. that mediates vasodilation, neurotransmission, and immune response. Due to its instability in biol. environments, NO-releasing small-mol. compounds have been developed for biol. experiments and also as therapeutic reagents for vascular diseases. Although photocontrollable NO releasers are very useful chem. tools because of their precise operability in response to light irradiation, their biol. applications have been limited, mainly because they require UV light irradiation or contain metal ions with the potential to cause cytotoxicity. In order to overcome these problems, our group has developed visible-light-responsive NO releasers based on photoreodox reaction. These compounds are composed of two moieties, an NO-releasing moiety and a light-harvesting antenna moiety. After photoirradiation, photoinduced electron transfer from the NO releasing moiety to the antenna takes place, followed by NO release. Based on this system, we developed a blue-light-controllable NO releaser and a yellowish-green-light-controllable one, which are applicable for cellular and ex vivo experiments This account focuses on recent developments in photoredox-driven NO releasers and their applications for spatiotemporally controlled NO release in cells and ex vivo.

Yuki Gosei Kagaku Kyokaishi published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Application In Synthesis of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Shie, Jiun-Jie published the artcileAn Azido-BODIPY Probe for Glycosylation: Initiation of Strong Fluorescence upon Triazole Formation, Quality Control of 26187-28-0, the publication is Journal of the American Chemical Society (2014), 136(28), 9953-9961, database is CAplus and MEDLINE.

The authors have designed a low fluorescent azido-BODIPY-based probe AzBOCEt (Az10) that undergoes copper(I)-catalyzed 1,3-dipolar cycloadditions with alkynes to yield strongly fluorescent triazole derivatives The fluorescent quantum yield of a triazole product T10 is enhanced by 52-fold as compared to AzBOCEt upon excitation at a wavelength >500 nm. Quantum mech. calculations indicate that the increase in fluorescence upon triazole formation is due to the lowering of the HOMO energy level of the aryl moiety to reduce the process of acceptor photoinduced electron transfer. AzBOCEt is shown to label alkyne-functionalized proteins in vitro and glycoproteins in cells with excellent selectivity, and enables cell imaging and visualization of glycoconjugates in alkynyl-saccharide-treated cells at extremely low concentration (0.1 μM). Furthermore, the alkyne-tagged glycoproteins from cell lysates can be directly detected with AzBOCEt in gel electrophoresis.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C8H6ClF3, Quality Control of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Elsom, L. F. published the artcilePyrrole studies. XIV. Spectroscopic characteristics of cyanopyrroles, COA of Formula: C7H8N2, the publication is Journal of the Chemical Society [Section] B: Physical Organic (1970), 79-81, database is CAplus.

Data for pyrroles containing Me and CN groups show that the NH stretching frequency may be represented by the equation: νNH(cm-1) = 3496 – 9nαMe + 2nβMe – 22nαCN – 12nβCN, where nα and nβ are the number of substituents in the α- and β-positions resp. The electronic spectra indicate that in the excited state the resonance stabilization by the α-CN group is greater than that of the β-CN group to the extent of about 10.5 kcal/mole.

Journal of the Chemical Society [Section] B: Physical Organic published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, COA of Formula: C7H8N2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Melent’eva, T. A. published the artcilePolarographic reduction of hydrobromides of dipyrrylmethenes, Related Products of nitriles-buliding-blocks, the publication is Zhurnal Obshchei Khimii (1972), 42(10), 2274-9, database is CAplus.

In I (R = Me, Et, CO2Et, NO2, CN, Ac, CH2CO2H), prepared by heating 2-formyl-3-acetyl-4-methyl-5-carbethoxypyrrole and pyrroles unsubstituted in the 2-position in the presence of HBr, the polarog. curves show a linear relation between halfwave potentials and the substituent constants The transmission of the substituent effect in the β-position with respect to dipyrrolylmethene chromophore occurs mainly through resonance. MeCOCH2CO2Et in AcOH, treated with aqueous NaNO2 and AcOH, followed by Zn dust and Et levulinate, gave 10% 2,4-dimethyl-3-carbethoxymethyl-5-carbethoxypyrrole, which with aqueous alc. NaOH gave the free dicarboxylic acid. The latter was heated with ethanolamine at 150° to give 2,4-dimethyl-3-carboxymethylpyrrole in 50% yield.

Zhurnal Obshchei Khimii published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ieda, Naoya published the artcilePhotomanipulation of Vasodilation with a Blue-Light-Controllable Nitric Oxide Releaser, Computed Properties of 26187-28-0, the publication is Journal of the American Chemical Society (2014), 136(19), 7085-7091, database is CAplus and MEDLINE.

Spatiotemporally controllable nitric oxide (NO)-releasers allow us to analyze the physiol. effects of NO, a gaseous mediator that modulates many biol. signaling networks, and are also candidate chemotherapeutic agents. We designed and synthesized a blue-light-controllable NO releaser, named NOBL-1, which bears an N-nitrosoaminophenol moiety for NO release tethered to a BODIPY dye moiety for harvesting blue light. Photoinduced electron transfer from N-nitrosoaniline to the antenna moiety upon irradiation with relatively noncytotoxic blue light (470-500 nm) should result in NO release with formation of a stable quinone moiety. NO release from NOBL-1 was confirmed by ESR spin trapping and fluorescence detection. Spatially controlled NO release in cells was observed with DAR-4M AM, a fluorogenic NO probe. We also demonstrated temporally controlled vasodilation of rat aorta ex vivo by blue-light-induced NO release from NOBL-1. This compound should be useful for precise examination of the functions of NO with excellent spatiotemporal control.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Computed Properties of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts