Category: 58610-61-0

Structure-Guided Design of Novel, Potent, and Selective Macrocyclic Plasma Kallikrein Inhibitors was written by Li, Zhe;Partridge, James;Silva-Garcia, Abel;Rademacher, Peter;Betz, Andreas;Xu, Qing;Sham, Hing;Hu, Yunjin;Shan, Yuqing;Liu, Bin;Zhang, Ying;Shi, Haijuan;Xu, Qiong;Ma, Xubo;Zhang, Li. And the article was included in ACS Medicinal Chemistry Letters in 2017.Quality Control of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate The following contents are mentioned in the article:

A series of macrocyclic analogs were designed and synthesized based on the cocrystal structure of small mol. plasma kallikrein (pKal) inhibitor, I, with the pKal protease domain. This led to the discovery of a potent macrocyclic pKal inhibitor II, with an IC₅₀ of 2 nM for one olefinic isomer and 42.3 nM for the other olefinic isomer. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Quality Control of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Quality Control of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel syntheses of camptothecin alkaloids. Part I. Intramolecular [4+2] cycloadditions of N-arylimidates and 4H-3,1-benzoxazin-4-ones as 2-aza-1,3-dienes was written by Fortunak, Joseph M. D.;Mastrocola, Antonietta R.;Mellinger, Mark;Sisti, Nicolas J.;Wood, Jeffery L.;Zhuang, Zhi-Ping. And the article was included in Tetrahedron Letters in 1996.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate The following contents are mentioned in the article:

Intramol. [4+2] cycloadditions of both N-arylimidates and (4H)-3,1-benzoxazin-4-ones acting as 2-aza-1,3-dienes were described. Reaction with unactivated alkynes lead to pyrrolo[3,4-b]quinolines containing the ABC ring system of camptothecin. E.g., 10-methoxycamptothecin precursor I was prepared by intramol. [4+2] cycloaddition of a 4:1 isomeric mixture of O-methylimidate II (R = 4-MeOC₆H₄), which had been prepared by Me₃OBF₄ O-methylation of the corresponding N-(4-methoxyphenyl)-amide, followed by elimination of methanol. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ路mol� in pyridine vs. 150 kJ路mol� in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel syntheses of camptothecin alkaloids. Part I. Intramolecular [4+2] cycloadditions of N-arylimidates and 4H-3,1-benzoxazin-4-ones as 2-aza-1,3-dienes was written by Fortunak, Joseph M. D.;Mastrocola, Antonietta R.;Mellinger, Mark;Sisti, Nicolas J.;Wood, Jeffery L.;Zhuang, Zhi-Ping. And the article was included in Tetrahedron Letters in 1996.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate The following contents are mentioned in the article:

Intramol. [4+2] cycloadditions of both N-arylimidates and (4H)-3,1-benzoxazin-4-ones acting as 2-aza-1,3-dienes were described. Reaction with unactivated alkynes lead to pyrrolo[3,4-b]quinolines containing the ABC ring system of camptothecin. E.g., 10-methoxycamptothecin precursor I was prepared by intramol. [4+2] cycloaddition of a 4:1 isomeric mixture of O-methylimidate II (R = 4-MeOC₆H₄), which had been prepared by Me₃OBF₄ O-methylation of the corresponding N-(4-methoxyphenyl)-amide, followed by elimination of methanol. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ路mol� in pyridine vs. 150 kJ路mol� in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel syntheses of camptothecin alkaloids. Part I. Intramolecular [4+2] cycloadditions of N-arylimidates and 4H-3,1-benzoxazin-4-ones as 2-aza-1,3-dienes was written by Fortunak, Joseph M. D.;Mastrocola, Antonietta R.;Mellinger, Mark;Sisti, Nicolas J.;Wood, Jeffery L.;Zhuang, Zhi-Ping. And the article was included in Tetrahedron Letters in 1996.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate The following contents are mentioned in the article:

Intramol. [4+2] cycloadditions of both N-arylimidates and (4H)-3,1-benzoxazin-4-ones acting as 2-aza-1,3-dienes were described. Reaction with unactivated alkynes lead to pyrrolo[3,4-b]quinolines containing the ABC ring system of camptothecin. E.g., 10-methoxycamptothecin precursor I was prepared by intramol. [4+2] cycloaddition of a 4:1 isomeric mixture of O-methylimidate II (R = 4-MeOC₆H₄), which had been prepared by Me₃OBF₄ O-methylation of the corresponding N-(4-methoxyphenyl)-amide, followed by elimination of methanol. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ路mol� in pyridine vs. 150 kJ路mol� in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel syntheses of camptothecin alkaloids. Part I. Intramolecular [4+2] cycloadditions of N-arylimidates and 4H-3,1-benzoxazin-4-ones as 2-aza-1,3-dienes was written by Fortunak, Joseph M. D.;Mastrocola, Antonietta R.;Mellinger, Mark;Sisti, Nicolas J.;Wood, Jeffery L.;Zhuang, Zhi-Ping. And the article was included in Tetrahedron Letters in 1996.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate The following contents are mentioned in the article:

Intramol. [4+2] cycloadditions of both N-arylimidates and (4H)-3,1-benzoxazin-4-ones acting as 2-aza-1,3-dienes were described. Reaction with unactivated alkynes lead to pyrrolo[3,4-b]quinolines containing the ABC ring system of camptothecin. E.g., 10-methoxycamptothecin precursor I was prepared by intramol. [4+2] cycloaddition of a 4:1 isomeric mixture of O-methylimidate II (R = 4-MeOC₆H₄), which had been prepared by Me₃OBF₄ O-methylation of the corresponding N-(4-methoxyphenyl)-amide, followed by elimination of methanol. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ路mol鈭? in pyridine vs. 150 kJ路mol鈭? in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Improved synthesis of 6-cyano-1-hydroxy-7-methyl-5-oxo-3,5-dihydro-indolizine-2-carboxylic acid methyl ester was written by Yang, Song;Zhang, Wannian;Zhou, Youjun;Yao, Jianzhong;Ji, Haitao. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2004.COA of Formula: C10H10N2O3 The following contents are mentioned in the article:

The synthesis of 6-cyano-1-hydroxy-7-methyl-5-oxo-3,5-dihydro-indolizine-2-carboxylic acid Me ester, an intermediate of the total synthesis of camptothecins, was improved. The yield of Et acetopyruvate was raised by controlling the speed of dropping and reaction time. The “one-pot procedure” was taken to prepare the title compound from Et acetopyruvate. The overall yield of the title compound was raised from 31% to 42.5%, and its structure of was confirmed by ¹H-NMR, MS and EA. The synthesis process was improved by the simplified operation, raised yield, shortened reaction time and the reduced usage of reagent. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0COA of Formula: C10H10N2O3).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. COA of Formula: C10H10N2O3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Antitumor agents. VI. Synthesis and antitumor activity of ring A-, ring B-, and ring C-modified derivatives of camptothecin was written by Sugimori, Masamichi;Ejima, Akio;Ohsuki, Satoru;Matsumoto, Kensuke;Kawato, Yasuyoshi;Yasuoka, Megumi;Tagawa, Hiroaki;Terasawa, Hirofumi. And the article was included in Heterocycles in 1994.Quality Control of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate The following contents are mentioned in the article:

Eleven ring A-, ring B-, and ring C-modified analogs of the antitumor alkaloid camptothecin (I) were prepared and evaluated for cytotoxicity and antitumor activity against P388 mouse leukemia. Among the six ring A-modified analogs, hexacyclic compound II retained the same order of activity as I. Most of the ring B- and ring C-modified analogs displayed greatly reduced activity, whereas compound III, which has an alkylidene group at position 5, was found to be as active as I. These results confirmed the necessity of the intact rings A, B, and C of I for antitumor activity. Further, the higher activity of II and III suggest that the “northern” part of the camptothecin mol. may be a suitable site for functionalization to obtain more potent analogs of I. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Quality Control of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. Pyridine has a conjugated system of six 蟺 electrons that are delocalized over the ring. The molecule is planar and, thus, follows the H眉ckel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Quality Control of Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Plant antitumor agents. 18. Synthesis and biological activity of camptothecin analogs was written by Wani, Mansukh C.;Ronman, Peter E.;Lindley, James T.;Wall, Monroe E.. And the article was included in Journal of Medicinal Chemistry in 1980.COA of Formula: C10H10N2O3 The following contents are mentioned in the article:

10-Methoxy, I (R = OMe); 1-aza-, benz[j]- and 18-methoxycamptothecin were obtained by total synthesis from II via III. The 2 water-soluble analogs, I (R = OCH₂CO₂H, OCH₂CH₂NEt₂) with intact ring E were prepared from natural I (R = OH). In general, there was a good correlation between in vitro 9KB cytotoxicity and activity in the P388 leukemia system. While the aza analog was active in P388 only at a much higher dose level than natural camptothecin (I, R = H), the 18-methoxy analog exhibited activity comparable to that of I (R = H). The water-soluble derivative I (R = OCH₂CO₂H) was inactive. I (R = OCH₂CH₂NEt₂).HCl showed excellent activity at a high dose level. This could be due to its hydrolysis to I (R = OH), (卤)-camptothecin was roughly half as active as I (R = H) indicating that the isomer is inactive. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0COA of Formula: C10H10N2O3).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine derivatives are also useful as small-molecule 伪-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.COA of Formula: C10H10N2O3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

β-Dicarbonyl compounds. V. The condensation of acetoneoxalic ester and O-ethylacetoneoxalic ester with cyanoacetamide was written by Henecka, Hans. And the article was included in Chemische Berichte in 1949.Formula: C10H10N2O3 The following contents are mentioned in the article:

Heating 8.4 g. NCCH₂CONH₂ (I) in 33 cc. H₂O with 16 g. AcCH:C(OH)CO₂Et (II) in 5 cc. EtOH and 0.5 cc. piperidine 6 hrs. on a water bath gives 14.7% Et 2-methyl-5-cyano-6(1H)-pyridone-4-carboxylate, CH:CMe.NH.CO.C(CN):CCO₂Et (III), leaflets, m. 208°. II (160 g.) is added dropwise to 84 g. I in 1200 cc. absolute EtOH and 450 cc. EtOH containing 23 g. Na, the mixture heated 6 hrs. at 60-5°, and the Na salt of III which seps. is dissolved in 2 l. H₂O; acidification of the solution gives 64.5% III, m. 213°. Dropwise addition of 160 g. II to 84 g. I in 2 l. boiling Me₂CO and 140 g. anhydrous K₂CO₃, refluxing the mixture 6 hrs., diluting with H₂O, and acidifying give 82.2% III. In the same way I and MeOCH₂COCH₂Ac give 81% 2-methyl-4-methoxymethyl-5-cyano-6(1H)-pyridone, m. 235-7°. Heating 50 g. III in 250 cc. POCl₃ with 50 g. PCl₅ 1 hr. on a water bath, distilling off the POCl₃ in vacuo at 30-40°, extracting the residue with CHCl₃, and distilling off the CHCl₃ in vacuo from the neutralized solution give 62.5% Et 2-methyl-5-cyano-6-chloro-4-pyridinecarboxylate (IV), b_2.5 144-6°, which soon crystallizes. Reduction of 10 g. IV in 200 cc. EtOH and 15 cc. concentrated HCl with Pd-charcoal in 150 cc. 0.1 N HCl and 9 g. charcoal (Merck) 24 hrs. with H gives 41.7% 2-methyl-5-aminomethyl-4-pyridinecarboxylic acid lactam, fine crystals, m. 244-6°. To a boiling mixture of 100 g. III in 750 cc. Me₂CO and 70 g. K₂CO₃, is added 62 g. Me₂SO₄ dropwise with stirring, the filtered solution evaporated, and the residue recrystallized from C₆H₆, giving 55.3% Et 1,2-dimethyl-5-cyano-6(1H)-pyridone-4-carboxylate, pale yellow crystals, m.135-6°, from C₆H₆. From the C₆H₆ mother liquor is isolated 20.6% Et 2-methyl-5-cyano-6-methoxy-4-pyridinecarboxylate, m. 75-6°. Boiling 84 g. I with 186 g. MeC(OEt):CHCOCO₂Et in the presence of 140 g. K₂CO₃ 14 hrs. gives 73% Et 4-methyl-5-cyano-6(1H)-pyridone-2-carboxylate (V), m. 235-7°. Treatment of V with POCl₃ gives 73.5% Et 4-methyl-5-cyano-6-chloro-2-pyridinecarboxylate (VI), b₃ 157°, m. 90-1°. Reduction of 5 g. VI in HCl 24 hrs. with H in the presence of Pd and treatment of the product with NaNO₂ at 60° give Et 4-methyl-5-hydroxymethyl-2-pyridine-carboxylate, fine crystals from CH₂Cl₂-petr. ether, m. 98-100°. The reaction mechanism of the condensation is explained on the basis of the electron theory. This study involved multiple reactions and reactants, such as Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0Formula: C10H10N2O3).

Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (cas: 58610-61-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Formula: C10H10N2O3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem