- A simple and environmentally benign synthesis of novel spiro[indoline-3,5′-pyrano[2,3-d]pyrimidine] derivatives in water
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Abstract: A green, convenient, and efficient one-pot synthesis of a new class of spiro[indolinepyranopyrimidine] derivatives was achieved in good yields by the multi-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine derived from the addition
- Ghadiri, Sakineh,Bayat, Mohammad,Hosseini, Fahimeh Sadat
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p. 1079 - 1084
(2019/03/14)
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- Rapid and catalyst free synthesis of new bis(benzo[: G] chromene) and bis(pyrano[3,2- c] chromene) derivatives and optimization of reaction conditions using response surface methodology
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4,4′-(1,4-phenylene)bis(2-(alkylamino)-3-nitro-4H-benzo[g]chromene-5,10-dione) and 4,4′-(1,4-phenylene)bis(2-(alkylamino)-3-nitropyrano[3,2-c]chromen-5(4H)-one) derivatives are synthesized by a one-pot, multi-component reaction of N-alkyl-1-(methylthio)-2
- Hosseini, Fahimeh Sadat,Bayat, Mohammad,Afsharnezhad, Milad
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p. 39466 - 39474
(2019/12/15)
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- Synthesis of Spiro[indoline-3,4′-pyrano[3,2-c]chromene]diones
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A new series of isatin-based spiro-fused derivatives were prepared, via three-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine derived from the addition of various amines to nitroketene dithioacetal with isatin derivatives and 4-hydroxycouma
- Ghadiri, Sakineh,Bayat, Mohammad,Hosseini, Fahimeh Sadat
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p. 2693 - 2697
(2018/10/20)
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- POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS
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Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.
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Paragraph 0633; 0634
(2016/08/17)
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- Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
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Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.
- Galkin, Konstantin I.,Krivodaeva, Elena A.,Romashov, Leonid V.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Burykina, Julia V.,Ananikov, Valentine P.
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supporting information
p. 8338 - 8342
(2016/07/19)
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- A 1 - methylamino -1 - methylthio -2 - nitroethylene method for the preparation of
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The invention relates to the field of chemical synthesis, and especially relates to a preparation method for 1-methylamino-1-methylthio-2-nitroethylene. The preparation method comprises: in the presence of a solvent, taking nitromethane, carbon disulfide and potassium hydroxide to perform a condensation reaction, so as to obtain a compound of a formula II; taking the compound of the formula II and methylamine to perform amination reaction, so as to obtain a compound of a formula III and hydrosulfide ion which is reacted with an acid for generating hydrogen sulfide; taking the compound of the formula III, a methylation reagent and an alkali to perform a methylation reaction, so as to obtain 1-methylamino-1-methylthio-2-nitroethylene crude product; and refining the crude product, so as to obtain 1-methylamino-1-methylthio-2-nitroethylene. The provided preparation method for 1-methylamino-1-methylthio-2-nitroethylene eliminates generation of a main gas pollution source methyl mercaptan, guarantees product quality, substantially reduces usage amount of the raw materials, shortens the reaction time and improves the product yield.
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Paragraph 0073; 0074; 0075; 0076; 0077
(2016/10/09)
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- An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
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A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K2CO3 in refluxing ethanol is descr
- Kumar, Sundaravel Vivek,Muthusubramanian, Shanmugam,Menéndez, J. Carlos,Perumal, Subbu
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supporting information
p. 1707 - 1712
(2016/04/10)
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- Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration
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On the basis of the structure of heterocyclic-fused cis configuration derivatives and chain-opening neonicotinoids, two series of novel chain-opening tetrahydropyridine analogues were designed and synthesized. The preliminary bioassay tests were determined on cowpea aphid (Aphis craccivora) and armyworm (Pseudaletia separata Walker). The results showed that some of the target compounds exhibited repellent effects, whereas others showed good insecticidal activities.
- Lu, Siyuan,Shao, Xusheng,Li, Zhong,Xu, Zhiping,Zhao, Shishuai,Wu, Yinli,Xu, Xiaoyong
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experimental part
p. 322 - 330
(2012/04/04)
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- Inhibitors for human glutaminyl cyclase by structure based design and bioisosteric replacement
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The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer's disease. The hallmark of this principle is the prevention of the formation of Aβ 3,11(pE)-40,42, as these Aβ-speci
- Buchholz, Mirko,Hamann, Antje,Aust, Susanne,Brandt, Wolfgang,B?hme, Livia,Hoffmann, Torsten,Schilling, Stephan,Demuth, Hans-Ulrich,Heiser, Ulrich
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experimental part
p. 7069 - 7080
(2010/05/02)
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- Synthesis and analgesic activity evaluation of some agmatine derivatives
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A series of N,N′-disubstituted-2-nitroethene-1,1-diamine and N,N′-disubstituted-N″-cyanoguanidine derivatives were prepared and evaluated for in vivo analgesic activity. The blood brain barrier (BBB) VolSurf model was used to predict the BBB permeation profiles of our synthesized compounds. Some compounds show both remarkable analgesic activity and good BBB permeation profiles, and these compounds might be developed for treatment of opioid tolerance and dependence.
- He, Hongxia,Liu, Mengjia,Zheng, Zhibing,Liu, Ying,Xiao, Junhai,Su, Ruibin,Hu, Chun,Li, Jin,Li, Song
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p. 393 - 402
(2007/10/03)
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- Second harmonic generation in push-pull ethylenes: Influence of chirality and hydrogen bonding
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The effect of chiral substituents and hydrogen bonding functional groups on the microscopic and macroscopic second-order non-linearities in some donor-acceptor substituted ethylenes has been investigated. It appears that extensive intramolecular and intermolecular hydrogen bonding helps to improve both the microscopic hyperpolarizability (β) as well as the powder second harmonic generation (SHG) efficiency in these compounds. The substitution of the chiral α-methylbenzylamine donor guarantees a non-centrosymmetric structure. Cocrystallization with triphenylphosphine oxide (TPPO) does not appear to yield better SHG efficiency in the α-methylbenzylamine substituted ethylene compound which has an extended hydrogen bonding network.
- Mohanalingam,Nethaji,Das, Puspendu Kumar
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p. 177 - 188
(2007/10/03)
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- Nitroketene-s,n-acetals as precursors for nitroacetamides and the elusive nitrothioacetahides
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1-Amino-1-methylthio-2-nitroethenes (2) can be converted in high yields to the Nitroacetamides (3) by Hg2+ catalysed hydrolysis and to the Nitrothioacetamides (4) by Na2S in ethanol-acetic acid.
- Manjunatha, Sulur G.,Reddy, K. Venodhar,Rajappa, Srinivasachari
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p. 1327 - 1330
(2007/10/02)
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- Zeolites in Organic Syntheses: A Novel Route to Functionalised Ketene S,N-Acetals
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Active methylene compounds react with bis(methylthio)alkaneimines in the presence of a zeolite catalyst to give functionalised ketene S,N-acetals in good yields.
- Deshmukh, Abdul Rakeeb A. S.,Reddy, T. Indrasena,Bhawal, Baburao M.,Shiralkar, Vasudeo P.,Rajappa, Srinivasachari
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p. 1217 - 1218
(2007/10/02)
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- MECHANISM OF H/D EXCHANGE AND VINYLIC SUBSTITUTION IN 2,2-DISUBSTITUTED NITROETHYLENE AND RELATED STUDIES
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Rate measurements for H/D exchange at the α-C atom of the nitroethylenic moiety in ranitidine, 2 (a histaminic H2-receptor antagonist with ulcerostatic activity), and in the model compounds 3a, 3b have revealed pseudo-first order, pH-dependent kinetics.These data have been interpreted in terms of an acid-catalysed intramolecular proton (deuterium) transfer within the nitrolic form of the compounds investigated with inversion of configuration at the carbon-carbon double bond.Qualitative studies of the rates of nucleophilic substitution at the vinylic β-C atom in 2,2-bismethylthio-1-nitroethylene (3a) and 2,2-bismethylthio-N-cyanoazomethine (4a) with methylamine, revealed inversion of the relative rates of the first and second substitution step.The result has been rationalized as due to a change from addition-elimination to β,γ-elimination-addition mechanism.HMO calculations of the ?-electron densities and ?-bond orders in 3a-3c and 4a-4c support this rationalization.
- Sega, Alessandro,Toso, Roberto,Sunjic, Vitomir,Klasinc, Leo,Sabljic, Aleksandar,Srzic, Dunja
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p. 217 - 222
(2007/10/02)
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- PROCESS FOR PREPARING 2-AMINO-2-ALKYLTHIO-1-NITROETHYLENE COMPOUNDS
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A process for preparing 2-amino-2-alkylthio-1-nitroethylene compounds by reacting a 1-lower alkylsulfinyl-1-lower alkylthio-2-nitroethylene with an amine. The products of the process are intermediates for the production of histamine H 2-antagonists.
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