Category: 75629-62-8

On November 27, 2003, Cai, Sui Xiong; Jiang, Songchun; Kemnitzer, William E.; Zhang, Hong; Attardo, Giorgio; Denis, Real published a patent.Related Products of 75629-62-8 The title of the patent was Preparation of substituted 4-aryl-4H-pyrrolo[2,3-h]chromenes and analogs as activators of caspases and inducers of apoptosis and their uses against cancer and other disorders. And the patent contained the following:

The present invention is directed to substituted 4-aryl-4H-pyrrolo[2,3-h]chromenes and analogs thereof (shown as I; variables defined below; e.g. II). The present invention also relates to the discovery that compounds I are activators of caspases and inducers of apoptosis. Therefore, I can be used to induce cell death in a variety of clin. conditions in which uncontrolled growth and spread of abnormal cells occurs. The ability to activate the caspase cascade and induce apoptosis in human breast cancer cell lines T-47D and ZR-75-1 was measured for ∼50 examples of I, e.g. EC50 (nM) = 2.3 and 1.6, resp., for II. Although the methods of preparation are not claimed, ∼50 example preparations are included. For I: R1 = alkyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, aminoalkyl and oxiranylalkyl; R3 and R4 = H, halo, haloalkyl, aryl, fused aryl, carbocyclic, a heterocyclic group, a heteroaryl group, C1-10 alkyl, alkenyl, alkynyl, arylalkyl, arylalkenyl, arylalkynyl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, carbocycloalkyl, heterocycloalkyl, hydroxyalkyl, aminoalkyl, carboxyalkyl, nitro, amino, cyano, acylamido, hydroxy, thiol, acyloxy, azido, alkoxy, carboxy, methylenedioxy, carbonylamido or alkylthio; R5 is H or C1-10 alkyl. A is (un)substituted and is aryl, heteroaryl, saturated carbocyclic, partially saturated carbocyclic, saturated heterocyclic, partially saturated heterocyclic or arylalkyl; D is (un)substituted and is a heteroaromatic, partially saturated (un)saturated heterocyclic fused ring, wherein said fused ring has 5 or 6 ring atoms, wherein one or two of said ring atoms are N atoms and the others of said ring atoms are C atoms. Y is CN, COR19, CO2R19 or CONR20R21, wherein R19, R20 and R21 = H, C1-10-alkyl, haloalkyl, aryl, fused aryl, carbocyclic, a heterocyclic group, a heteroaryl group, alkenyl, alkynyl, arylalkyl, arylalkenyl, arylalkynyl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, carbocycloalkyl, heterocycloalkyl, hydroxyalkyl or aminoalkyl; or R20 and R21 are taken together with the N to form a heterocycle; and Z is NR22R23, NHCOR22N(COR23)2, N(COR22)(COR23), N:CHOR19 or N:CHR19 wherein R22 and R23 = H, C1-4 alkyl or aryl, or R22 and R23 are combined together with the group attached to them to form a heterocycle. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Related Products of 75629-62-8

The Article related to aryl pyrrolochromene analog preparation caspase activator apoptosis inducer, antitumor agent aryl pyrrolochromene analog preparation pharmaceutical composition, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Related Products of 75629-62-8

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On May 18, 2018, Guchhait, Sankar K.; Sisodiya, Shailendra; Saini, Meenu; Shah, Yesha V.; Kumar, Gulshan; Daniel, Divine P.; Hura, Neha; Chaudhary, Vikas published an article.Application In Synthesis of 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Synthesis of Polyfunctionalized Pyrroles via a Tandem Reaction of Michael Addition and Intramolecular Cyanide-Mediated Nitrile-to-Nitrile Condensation. And the article contained the following:

A new approach for the synthesis of tetrasubstituted/functionalized NH-pyrroles from gem-diactivated acrylonitriles and TMSCN has been developed. The strategy utilizes the generation of vic-dinitrile via Michael addition and cyanide-mediated nitrile-to-nitrile cyclocondensation, which proceed in tandem guided by manifold roles of “CN”. An extended application to the production of fused pyrrole has also been realized. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Application In Synthesis of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to diactivated acrylonitrile trimethylsilyl cyanide tandem michael addition cyclocondensation, pyrrole polyfunctionalized preparation, Heterocyclic Compounds (One Hetero Atom): Pyrroles and Pyrrolizines and other aspects.Application In Synthesis of 2-((1H-Indol-3-yl)methylene)malononitrile

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On April 30, 2003, Ali, Gameel A. M. El-Hag published an article.Name: 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Studies on Thiazolopyridines. Part 3: Reactivity of Thiazolo[3,2-a]-3-aza[1,8]naphthyridine Towards Some Nucleophiles. And the article contained the following:

A variety of new thiazolo[3,2-a]pyridine derivatives having 3-indolyl group were produced by refluxing thiazolinone derivative with different benzylidenemalononitrile derivatives Reactivity of Thiazolo[3,2-a]-3-aza[1,8]naphthyridine (I) toward some nitrogen nucleophiles was investigated. Thus, the novel pyrazoles were obtained when I was allowed to react with hydrazine and Ph hydrazine in ethanol under reflux. On the other hand, pyrazolo[3′,4′:4,5]thiazolo[3,2-a]-3-aza[1,8]naphthyridine was formed by condensation of I with benzoyl hydrazine. Finally, condensed heterocyclic compounds containing pyran rings were obtained by treatment I with active ethylene compounds Antimicrobial activity of some of the product was also evaluated. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Name: 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to thiazolopyridine derivative preparation reactivity nucleophile antimicrobial activity, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Name: 2-((1H-Indol-3-yl)methylene)malononitrile

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On May 5, 2016, Franconetti, A.; Dominguez-Rodriguez, P.; Lara-Garcia, D.; Prado-Gotor, R.; Cabrera-Escribano, F. published an article.Formula: C12H7N3 The title of the article was Native and modified chitosan-based hydrogels as green heterogeneous organocatalysts for imine-mediated Knoevenagel condensation. And the article contained the following:

A variety of methylenemalononitriles and Et cyanoacrylates derived from both aromatic and heteroaromatic aldehydes were synthesized by Knoevenagel condensation catalyzed with native and modified chitosan-based heterogeneous catalysts. The efficiency of our hydrogel organocatalysts, chitosan hydrogel beads and ureidyl-chitosan derivative hydrogel disks, was evaluated as function of pH, temperature and catalyst concentration by considering reaction rates, conversions, E/Z stereoselectivities, and kinetic studies of a model reaction between 4-nitrobenzaldehyde and Et cyanoacetate. An unprecedented study by solid state 13C CP MAS NMR of the employed catalyst when reaction was quenched after a 50% of conversion, has demonstrated that an imine-chitosan intermediate is formed during this process. Anal. of E/Z Et cyanoacrylate isomer mixtures for determining the corresponding stereoselectivity was carried out by NMR measuring carbon-proton coupling constants (3JC,H) using a novel CLIP-HSQMCB experiment Addnl., DFT calculations let us rationalize the observed E/Z stereoselectivities as well as to evaluate the role of ureidyl moiety on interaction with aldehydes and imine intermediate formation with chitosan derivative The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Formula: C12H7N3

The Article related to aromatic aldehyde knoevenagel condensation chitosan hydrogel organocatalyst, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Formula: C12H7N3

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On December 28, 2018, Bahuguna, Ashish; Kumar, Ashwani; Chhabra, Tripti; Kumar, Ajay; Krishnan, Venkata published an article.Name: 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Potassium-Functionalized Graphitic Carbon Nitride Supported on Reduced Graphene Oxide as a Sustainable Catalyst for Knoevenagel Condensation. And the article contained the following:

A nanocomposite of potassium-functionalized graphitic carbon nitride (KGCN) and reduced graphene oxide (RGO) was fabricated by a facile hydrothermal method and used as a heterogeneous catalyst for Knoevenagel condensation and sustainable synthesis of aryl substituted chromenes. The prepared KGCN-RGO nanocomposite catalyst has been characterized by using various techniques, such as powder X-ray diffraction technique (PXRD), Fourier transform IR spectroscopy, SEM, transmission electron microscopy, thermogravimetric anal., and BET surface area anal. After detailed characterization, the nanocomposite was used as a heterogeneous catalyst to synthesize various aryl substituted chromenes in ethanol. The developed KGCN-RGO nanocatalyst also rendered good recyclability for the explored catalytic reactions. In addition, a high value of atom economy and a low value of E-factor are also key highlights of this green and sustainable catalytic protocol. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Name: 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to potassium functionalized graphitic carbon nitride knoevenagel condensation catalyst, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Name: 2-((1H-Indol-3-yl)methylene)malononitrile

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Jain, Shubha; Reddy, B. Nagi; Rao, K. Sambasiva; Neeliah, G. published an article in 2010, the title of the article was Microwave assisted synthesis of indole substituted alkenes using Knoevenagel condensation reaction and their antibacterial activity study.Computed Properties of 75629-62-8 And the article contains the following content:

The reaction rate of the Knoevenagel condensation can be dramatically enhanced by irradiating the reaction mixture containing an 3-indolealdehyde, active methylene compound, L-proline and PhCl using a com. microwave oven. Several Knoevenagel condensation products were synthesized within 5-17 min in good yields. The new compounds were also screened for antibacterial activity. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Computed Properties of 75629-62-8

The Article related to indole active methylene knoevenagel condensation microwave, indolyl alkene preparation antibacterial, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Computed Properties of 75629-62-8

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Lega, D. A.; Chernykh, V. P.; Shemchuk, L. A. published an article in 2016, the title of the article was The study of the three-component interaction between 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2 dioxide, hetarylcarbaldehydes and active methylene nitriles.HPLC of Formula: 75629-62-8 And the article contains the following content:

Some peculiarities of the three-component reaction of 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide with active methylene nitriles and hetarylcarbaldehydes have been described in this article. It has been found that if malononitrile is used, the products of the three-component reaction are 2-amino-4-hetaryl-3-cyano-6-ethyl-4,6- dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxides irresp. of the hetaryl fragment nature in the initial aldehyde. When using Et cyanoacetate as an active methylene nitrile instead of malononitrile the reaction lost its selectivity. In this case, depending on the hetarylcabaldehyde, three different types of products were obtained, namely, 2-amino-3-alkoxycarbonyl-4-hetaryl-4H-pyrans (for pyridine-3-, pyridine-4-carbaldehydes, and furan-2-carbaldehyde), triethylammonium salt of bis(1-ethyl-1H-2,1-benzothiazin-2,2- dioxo-4-ol-3-yl)(2-thienyl)methane (for thiophen-2-carbaldehyde) or Et 2-cyano-3-(1H-indol-3-yl)acrylate (for indole-3-carbaldehyde). Formation of a stable triethylammonium salts was considered as the process competitive with formation of 2-amino-4H-pyrans. This has allowed us to propose the modified mechanism of 2-amino-4H-pyran formation. This mechanism includes formation of triethylammonium salts of bis-adducts. According to this mechanism 2-amino-3-ethoxycarbonyl-4-(2-thienyl)-4H-pyran without any impurity of bis-adduct could be selectively obtained using the three-component reaction. Triethylammonium salts of bis-adducts were obtained by direct reaction of 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide with hetarylcarbaldehydes in the presence of equimolar amounts of triethylamine. It has been shown that the three-component reaction of 1-ethyl-1H-2,1-benzothiazM(3H)-one 2,2-dioxide with active methylene nitriles and hetarylcarbaldehydes is a more effective tool for obtaining fused 2-amino-4-hetaryl-4H-pyrans compared to the stepwise approach. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).HPLC of Formula: 75629-62-8

The Article related to three component reaction ethylbenzothiazinone dioxide hetarylcarbaldehyde nitrile, Physical Organic Chemistry: Ring Formation, Cleavage, Enlargement, and Contraction and other aspects.HPLC of Formula: 75629-62-8

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On June 30, 2007, Abd El-Latif, Nehad A.; Amr, Abd El-Galil E.; Ibrahiem, Alhusain A. published an article.Formula: C12H7N3 The title of the article was Synthesis, reactions, and pharmacological screening of heterocyclic derivatives using nicotinic acid as a natural synthon. And the article contained the following:

A series of substituted pyridine derivatives were prepared from 3-acetylpyridine, which was prepared from the corresponding nicotinic acid as a natural starting material. Reaction of 3-acetylpyridine with indole-3-carboxaldehyde afforded the corresponding 3-β-(3-indolyl)(acryloyl)pyridine, which was treated with hydroxylamine hydrochloride in pyridine or acetic acid in the presence of sodium acetate to afford 3-β-(3-indolyl)(acryloyl)pyridine oxime and oxazole derivatives The oxime was treated with Et isothiocyanate or toluene-3,5-diisocyanate in refluxing dioxane to give the corresponding Et thiosemicarbazide and 3,5-bis(semicarbazide) derivative 3-β-(3-Indolyl)(acryloyl)pyridine was condensed with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to give a cyano(amino)pyran derivative, while it was condensed with Et cyanoacetate or malononitrile in the presence of ammonium acetate to yield (cyano)pyridone and cyano(amino)pyridine derivatives Cyclization of (acryloyl)pyridine with o-phenylenediamine in refluxing butanol led to the formation of the corresponding benzodiazepine via the intermediate A. Finally, cycloaddition reaction of (acryloyl)pyridine with thiourea yielded thioxopyrimidine, which was treated with chloroacetic acid to yield thiazolopyrimidine. An arylmethylene derivative was prepared by reacting thiazolopyrimidine with indole-3-carboxaldehyde or by treating thioxopyrimidine with indole-3-carboxaldehyde and chloroacetic acid in one step. The pharmacol. screening showed that many of the compounds thus prepared have good analgesic and anticonvulsant activities comparable to valdecoxib [i.e, 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide] and carbamazepine as reference drugs. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Formula: C12H7N3

The Article related to nicotinic acid indolecarboxaldehyde thioxopyrimidine preparation analgesic anticonvulsant, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Formula: C12H7N3

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On December 31, 2018, Dyachenko, V. D.; Matusov, I. O.; Dyachenko, I. V.; Nenajdenko, V. G. published an article.Reference of 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Knoevenagel Reactions of Indole-3-carbaldehyde. Synthesis of 3-Substituted Indole Derivatives. And the article contained the following:

The Knoevenagel condensations of 1H-indole-3-carbaldehyde with various CH acids gave a number of substituted 3-(1H-indol-3-yl)acrylonitriles and acrylamides which were alkylated to afford the corresponding N-alkyl derivatives I [R = CN, CO2(CH2)6CH3, C(O)NHc-Pr; R1 = Me, allyl, Bn, etc.]. The latter were used as Michael acceptors in the synthesis of 4H-pyran, pyridine, 5,6,7,8-tetrahydroquinoline and [1,3]thiazolo[3,2-a]pyridine derivatives containing an indole fragment. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Reference of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to indole preparation, nitrile indole knoevenagel condensation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Reference of 2-((1H-Indol-3-yl)methylene)malononitrile

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On July 31, 2018, Honarmand, M.; Givzad, M. published an article.Recommanded Product: 75629-62-8 The title of the article was An efficient and eco-friendly process for the Knoevenagel reaction using nano organosalt catalyst. And the article contained the following:

A novel nano organosalt was synthesized easily by the reaction of sulfuric acid with 1,3-diaminopropane in water. The morphol. and structure of the synthesized organosalt were determined by various techniques. The catalytic application of organosalt was investigated in the Knoevenagel reaction of aryl/heteroaryl/alkyl aldehydes with activated methylene compounds under solvent-free conditions. The Knoevenagel products were obtained in high to excellent yields in the short reaction times. No toxic solvents and byproducts were involved, and in most cases no tedious purifications were needed. The catalyst was also recovered and reused after the five reaction cycles without a significant decrease in catalytic activity. The TEM image and elemental anal. of the recovered catalyst were confirmed the high stability and durability of nano organosalt under the applied reaction conditions. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Recommanded Product: 75629-62-8

The Article related to knoevenagel reaction nano organosalt catalyst eco friendly process, Industrial Organic Chemicals, Leather, Fats, and Waxes: Manufacture Of Industrial Organic Chemicals and other aspects.Recommanded Product: 75629-62-8

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