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(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is an organic compound characterized by its unique molecular structure, featuring a 2-en-1-one functional group, a dimethylamino group, and a 3-pyridyl group. (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is known for its potential applications in the synthesis of various organic molecules and pharmaceutical agents.

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  • 123367-26-0 Structure
  • Basic information

    1. Product Name: (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one
    2. Synonyms: (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one;(E)-3-(Dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one;(2E)-3-(DiMethylaMino)-1-(pyridin-3-yl)prop-2-en-1-one;(2E)-3-(DiMethylaMino)-1-(3-pyridyl)prop-2-en-1-one (IMpurity of Nilotinib);Nilotinib IMpurity ((2E)-3-(DiMethylaMino)-1-(3-pyridyl)prop-2-en-1-one)
    3. CAS NO:123367-26-0
    4. Molecular Formula: C10H12N2O
    5. Molecular Weight: 176.21508
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 123367-26-0.mol
  • Chemical Properties

    1. Melting Point: 113℃
    2. Boiling Point: 281℃
    3. Flash Point: 124℃
    4. Appearance: /
    5. Density: 1.070
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
    9. PKA: 4.74±0.70(Predicted)
    10. CAS DataBase Reference: (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one(CAS DataBase Reference)
    11. NIST Chemistry Reference: (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one(123367-26-0)
    12. EPA Substance Registry System: (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one(123367-26-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 123367-26-0(Hazardous Substances Data)

123367-26-0 Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is used as a reagent for the synthesis of oxindole-linked indolyl-pyrimidine derivatives, which are potential cytotoxic agents. These derivatives have shown promise in the development of new drugs for the treatment of cancer and other diseases, due to their ability to inhibit the growth and proliferation of cancer cells.
Used in Organic Chemistry Research:
In addition to its pharmaceutical applications, (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is also utilized in organic chemistry research for the synthesis of various organic compounds and the study of reaction mechanisms. Its unique structure allows for the exploration of new synthetic pathways and the development of innovative chemical processes.

Check Digit Verification of cas no

The CAS Registry Mumber 123367-26-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,3,3,6 and 7 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 123367-26:
(8*1)+(7*2)+(6*3)+(5*3)+(4*6)+(3*7)+(2*2)+(1*6)=110
110 % 10 = 0
So 123367-26-0 is a valid CAS Registry Number.

123367-26-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (Y0001695)  Imatinib impurity A  EuropePharmacopoeia (EP) Reference Standard

  • 123367-26-0

  • Y0001695

  • 1,880.19CNY

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123367-26-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-3-(Dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

1.2 Other means of identification

Product number -
Other names (2E)-3-(Dimethylamino)-1-(3-pyridinyl)-2-propen-1-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123367-26-0 SDS

123367-26-0Relevant articles and documents

Phenylamino-pyrimidine (PAP) - Derivatives: A new class of potent and highly selective PDGF-Receptor autophosphorylation inhibitors

Zimmermann, Juerg,Buchdunger, Elisabeth,Mett, Helmut,Meyer, Thomas,Lydon, Nicholas B.,Traxler, Peter

, p. 1221 - 1226 (1996)

Phenylamino-pyrimidines represent a novel class of inhibitors of the PDGF-receptor autophosphorylation with a high degree of selectivity versus other tyrosine and serine/threonine kinases. Optimum activity of ca 10 nM (IC50) was observed when the phenylamino-group which is attached to the pyrimidine carries a benzamide-moiety with a lipophilic substituent in 4-position. Copyright

Discovery of N-(2-Aminophenyl)-4-[(4-pyridin-3-ylpyrimidin-2-ylamino) methyl]benzamide(MGCD0103), an orally active histone deacetylase inhibitor

Zhou, Nancy,Moradei, Oscar,Raeppel, Stephane,Leit, Silvana,Frechette, Sylvie,Gaudette, Frederic,Paquin, Isabelle,Bernstein, Naomy,Bouchain, Giliane,Vaisburg, Arkadii,Jin, Zhiyun,Gillespie, Jeff,Wang, James,Fournel, Marielle,Yan, Pu T.,Trachy-Bourget, Marie-Claude,Kalita, Ann,Lu, Aihua,Rahil, Jubrail,MacLeod, A. Robert,Li, Zuomei,Besterman, Jeffrey M.,Delorme, Daniel

, p. 4072 - 4075 (2008)

The design, synthesis, and biological evaluation of N-(2-aminophenyl)-4- [(4-pyridin-3-ylpyrimidin-2-ylamino)methyl]benzamide 8 (MGCD0103) is described. Compound 8 is an isotype-selective small molecule histone deacetylase (HDAC) inhibitor that selectively inhibits HDACs 1-3 and 11 at submicromolar concentrations in vitro. 8 blocks cancer cell proliferation and induces histone acetylation, p21ciP/waf1 protein expression, cell-cycle arrest, and apoptosis. 8 is orally bioavailable, has significant antitumor activity in vivo, has entered clinical trials, and shows promise as an anticancer drug.

Imatinib intermediate as a two in one dual channel sensor for the recognition of Cu2+ and I- ions in aqueous media and its practical applications

Patil, Samadhan R.,Nandre, Jitendra P.,Jadhav, Devising,Bothra, Shilpa,Sahoo,Devi, Manisha,Pradeep, Chullikkattil P.,Mahulikar, Pramod P.,Patil, Umesh D.

, p. 13299 - 13306 (2014)

An imatinib intermediate, 6-methyl-N-[4-(pyridin-3-yl)pyrimidin-2-yl] benzene-1,3-diaminepyridopyrimidotoluidine (PPT-1), was developed for the colorimetric sensing of Cu2+ ions in aqueous solution. With Cu 2+, the receptor PPT-1 showed a highly selective naked-eye detectable color change from colorless to red over the seventy other tested cations. The colorimetric sensing ability of PPT-1 was successfully utilized in the preparation of test strips and supported silica for the real samples analysis to detect Cu2+ ions from 100% aqueous environment. Moreover, the iodide-sensing ability of receptor PPT-1 was explored among the ten examined anions.

Urea derivatives of STI571 as inhibitors of Bcr-Abl and PDGFR kinases

Manley, Paul W.,Breitenstein, Werner,Brüggen, Josef,Cowan-Jacob, Sandra W.,Furet, Pascal,Mestan, Jürgen,Meyer, Thomas

, p. 5793 - 5797 (2004)

Urea-based analogues of STI571 are described possessing structural features which can differentiate between Abl/Bcr-Abl and PDGFR kinase inhibition. The constitutively active Abl kinase activity of the Bcr-Abl oncoprotein is causative for chronic myelogenous leukemia. Urea derivatives, structurally related to the therapeutic agent STI571, have been identified, which potently inhibit the tyrosine kinase activity of recombinant Abl. In particular a dimethylamino-aniline derivative (18) inhibited c-Abl transphosphorylation with an IC50 value of 56 nM. Although this activity was not translated into cellular activity against the constitutively activated oncogenic Bcr-Abl, a number of compounds from this series potently inhibited cellular PDGFR autophosphorylation. It was also possible to differentiate between c-Abl and PDGFR kinase inhibition, with compound 22 being selective towards Abl and 23 selective for PDGFR.

New bis-, tris- and tetrakis(pyrazolyl)borate ligands with 3-pyridyl and 4-pyridyl substituents: Synthesis and coordination chemistryt

Adams, Harry,Batten, Stuart R.,Davies, Graham M.,Duriska, Martin B.,Jeffery, John C.,Jensen, Paul,Lu, Jinzhen,Motson, Graham R.,Coles, Simon J.,Hursthouse, Michael B.,Ward, Michael D.

, p. 1910 - 1923 (2005)

The new ligands dihydrobis[3-(4-pyridyl)pyrazol-1-yl]borate [Bp 4ph]-, hydrotris[3-(4-pyridyl)pyrazol-1-yl]borate [Tp 4py]-, tetrakis[3-(4-pyridyl)pyrazol-l-yl]borate [Tkp 4py]-, dihydrobis[3-(3-pyridyl)pyrazol-l-yl]borate [Bp 3py]-, hydrotris[3-(3-pyridyl)pyrazol-1-yl]borate [Tp 3py]- and tetrakis[3-(3-pyridyl)pyrazol-l-yl]borate [Tkp 48]- are derivatives of the well known bis-, tris- and tetrakis-(pyrazolyl)borate cores, bearing 4-pyridyl or 3-pyridyl substituents attached to the pyrazolyl C3 positions. These pyridyl groups cannot chelate to the metal ions in the poly(pyrazolyl) cavity but are externally directed. Structural studies on a range of metal complexes show how, in many cases, coordination of these pendant pyridyl groups to the M(pyrazolyl) n core of an adjacent metal complex fragment results in formation of coordination oligomers or polymeric networks. [Tl(Bp3py)], [Tl(Bp4ph)] and [Tl(Tp4py] form one-dimensional polymeric chains via coordination of one of their pendant pyridyl units to the Tl(I) centre of an adjacent complex fragment; in contrast, in [Tl(Tp3py)] coordination of all three pendant pyridyl units to separate Tl(I) neighbours results in formation of a two-dimensional polymeric sheet. In [Tl(Tkp 3py)] and [Tl(Tkp4py)] the Tl(I) is coordinated by two or three of the four pyrazolyl arms, respectively; bridging interactions of pendant 4-pyridyl groups with adjacent Tl(I) centres result in a two-dimensional sheet forming in each case. In Ag(Tkp4py) each Ag(I) ion is coordinated by two pyrazolyl rings, and two bridging pyridyl ligands from other complex units, resulting in a one-dimensional chain consisting of pairs of cross-linked zigzag chains. In contrast to these polymeric coordination networks, the structures of [Cu(Tp4py)] and [(Tp3py)Cd(CH3CO2)] are dimers, with a pendant pyridyl residue from the first metal centre attaching to a vacant coordination site on the second, and vice versa; these dimers are stabilised by π-stacking interactions between sections of the two ligands. [Ni(Tp3py)2] is monomeric, with an octahedral coordination geometry arising from two tris(pyrazolyl)borate chelates; the array of pendant 3-pyridyl groups is involved only in intramolecular hydrogen-bonding. [(Tp 4py)Re(CO)3] is also monomeric, with & facial arrangement of three pyrazolyl ligands and three carbonyls, with the pendant 4-pyridyl groups not further coordinated. [(Tp3py)Re(CO) 3], based on the related ligand hydrotris[3-(2-pyridyl)pyrazol-1-yl] borate, has a similar fac-(CO)3(pyrazolyl)3 coordination geometry. The Royal Society of Chemistry 2005.

Synthesis and muscarinic activities of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives

Plate, Ralf,Plaum, Marc J. M.,De Boer, Thijs,Andrews, John S.,Rae, Duncan R.,Gibson, Sam

, p. 227 - 237 (1996)

A series of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives (B) was synthesized and tested for muscarinic activity in receptor binding assays using [3H]-oxotremorine-M (3H-OXO-M) and [3H]-pirenzepine (3H-PZ) as ligands. Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies measuring their potencies to inhibit the binding of 3H-OXO-M and 3H-PZ. Preferential inhibition of 3H-OXO-M binding was used as an indicator for potential muscarinic agonistic properties; this potential was confirmed in functional studies on isolated organs. All compounds with agonistic properties showed 3H-PZ/3H-OXO-M potency ratios in excess of 20. In contrast, for antagonists this ratio was found to be close to unity. Mono-halogenation resulted in compounds (4b and 4d) with M3 agonistic properties as shown by their atropine sensitive stimulant properties in the guinea pig ileum, but with very little or no M1 activity. Some minor in vivo effects were observed for both these compounds, with the iodinated compound 4d inducing salivation. Compound 4d also showed some positive mnemonic properties in rats where spatial short-term memory had been compromised by temporary cholinergic depletion. These data indicate that some M3 agonism may be desired in therapeutic agents aimed at the treatment of the cognitive deficits of Alzheimer's disease patients.

Acid-base profiling of imatinib (Gleevec) and its fragments

Szakács, Zoltán,Béni, Szabolcs,Varga, Zoltán,?rfi, László,Kéri, Gy?rgy,Noszál, Béla

, p. 249 - 255 (2005)

The site-specific basicities of imatinib (Gleevec, a new signal transduction inhibitor drug of chronic myeloid leukemia) and two of its fragment compounds were quantitated in terms of protonation macroconstants, microconstants, and group constants by NMR-pH and pH-potentiometric titrations. Sequential protonation of imatinib follows the N34, N11, N31, N13 order, in which N11 and N31 show commensurable basicity, but negligible intramolecular interaction. Fragment compounds include two "halves" of imatinib, and their moiety-specific basicities confirm the NMR-based protonation sequence of the parent compound. NMR-pH profiles, macro- and/or microscopic protonation schemes, and species-specific distribution diagrams are presented. On the basis of these data, imatinib is shown to be predominantly neutral, monocationic, and tricationic at intestinal, blood, and gastric pH, respectively. The molecular hypotheses on imatinib binding to the Bcr-Abl oncogene fusion protein are interpreted at the site-specific level in view of the moiety basicities of imatinib.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Platte, Simon,Korff, Marvin,Imberg, Lukas,Balicioglu, Ilker,Erbacher, Catharina,Will, Jonas M.,Daniliuc, Constantin G.,Karst, Uwe,Kalinin, Dmitrii V.

supporting information, p. 3672 - 3690 (2021/08/07)

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

Huo, Xian-Sen,Jian, Xie-Er,Ou-Yang, Jie,Chen, Lin,Yang, Fang,Lv, Dong-Xin,You, Wen-Wei,Rao, Jin-Jun,Zhao, Pei-Liang

, (2021/05/10)

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

Method for preparing N-(5-carboxyl-2-methylphenyl)-4-(3-pyridine)-2-pyrilamine

-

Paragraph 0035; 0036, (2021/05/05)

The invention discloses a method for preparing N-(5-carboxyl-2-methylphenyl)-4-(3-pyridine)-2-pyrilamine. The method specifically comprises the following steps: step 1, carrying out ethyl esterification reaction on 3-nitro-4-methyl benzoic acid serving as an initial raw material to generate a compound 2; step 2, reducing nitro of the compound 2 through hydrogenation reduction reaction in the presence of palladium on carbon to generate a compound 3; step 3, reacting the compound 3 with a nitrile amine aqueous solution, and then carrying out base exchange to obtain a compound 4; step 4, carrying out cyclization between the compound 4 and a compound 6 to obtain a compound 7; and step 5, hydrolyzing the compound 7 under the action of an alkaline to generate a compound 8, namely N-(5-carboxyl-2-methylphenyl)-4-(3-pyridine)-2-pyrilamine. The method overcomes the defects that in the prior art such as long reaction time, low yield, high cost, difficulty for industrial production, and the like. A preparation method, which is high in yield, is environmentally-friendly, and is suitable for industrial production, is provided.

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