- Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
-
In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi
-
supporting information
p. 5905 - 5911
(2021/07/12)
-
- Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine
-
Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.
- Borate, Kailaskumar,Choi, Kyoungmin,Goetz, Roland,Hartwig, John F.,Shinde, Harish,Wang, Justin Y.,Zuend, Stephan J.
-
supporting information
p. 399 - 408
(2020/10/29)
-
- Synthesis, insecticidal activities, and structure-activity relationship of phenylpyrazole derivatives containing a fluoro-substituted benzene moiety
-
Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella. Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L-1, while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10-5 mg L-1 was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf, which further confirmed that ryanodine receptor (RyR) was its potential target.
- Gao, Li,Li, Huangong,Li, Yuxin,Li, Zhengming,Ma, Yi,Meng, Fanfei,Sun, Binqiao,Sun, Pengwei,Xie, Yongtao,Xiong, Lixia,Yang, Na,Zhang, Yan,Zhao, Yangyang,Zhou, Sha
-
p. 11282 - 11289
(2020/11/09)
-
- PROCESS FOR THE SYNTHESIS OF ARYL HYDRAZINES
-
The invention relates to a process for the synthesis of aryl hydrazinesof formula I or a salt thereof, which process comprises subjecting an arene of formula II to a coupling reaction with hydrazine or a derivative thereof, wherein the coupling reaction is conducted in the presence of a catalyst comprising palladium and a diphosphine ligand, wherein the phosphorus atoms are connected through two, three, four, or five atoms selected from car- bon, nitrogen, oxygen or iron, and in which the non-connecting phosphorus substituents are C1- C 10-alkyl or C3-C10-cycloalkyl, wherein the amount of Pd used is up to 0.5 mol-% relative to the amount of arene of formula II; and a base.
- -
-
Page/Page column 22; 24; 25
(2020/06/01)
-
- Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines
-
In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.
- Dey, Raghunath,Kumar, Pankaj,Banerjee, Prabal
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p. 5438 - 5449
(2018/05/28)
-
- Preparation method of 4-fluorophenylhydrazine hydrochloride
-
The invention relates to a preparation method of 4-fluorophenylhydrazine hydrochloride. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, reaction liquid is kept at strong acidity with concentrated hydrochloric acid to guarantee successful and complete reaction; in the reduction step, zinc powder-concentrated hydrochloric acid is used as a reducing agent and replaces sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, so that the reducing property is high, the yield is high, and the reaction time is shortened; impurities, such as zinc hydroxide, which are generated after reaction are convenient to remove, so that the number of product impurities is small, and the purity is high; in the salification step, leaching is carried out with acetone, so that the purity of a product is improved, and the appearance of the product is guaranteed. The preparation method is stable and reliable in process, easy to operate and high in product purity (the content measured based on high performance liquid chromatography is greater than or equal to 99 percent); the yield is greater than or equal to 39 percent, so that the requirement of the market for the 4-fluorophenylhydrazine hydrochloride can be completely met.
- -
-
Paragraph 0017-0024
(2017/06/20)
-
- Preparation method for 4-fluorophenylhydrazine phosphate
-
The invention relates to a preparation method for 4-fluorophenylhydrazine phosphate. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, concentrated hydrochloric acid is adopted for maintaining a reaction liquid in strong acidity, and guaranteeing smooth and complete reaction. In the step of reduction, zinc powder-concentrated hydrochloric acid is adopted as a reducing agent for replacing sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, the reducing property is good, the yield coefficient is high, the reaction time is shortened, impurities such as zinc hydroxide generated after reaction can be removed conveniently, the product impurities are small, and the purity is high. In the step of salification, acetone is adopted for elution, the product purity is increased, and the product appearance is guaranteed. According to the preparation method, the process is stable and reliable, operation is easy, the product purity is high (the content of the 4-fluorophenylhydrazine phosphate is measured through high performance liquid chromatography and is no smaller than 99.2%), the yield coefficient is no smaller than 42%, and the market demand for the 4-fluorophenylhydrazine phosphate can be fully met.
- -
-
Paragraph 0037-0046
(2017/06/20)
-
- Preparation method of 4-fluorophenylhydrazine oxalate
-
The invention relates to a preparation method of 4-fluorophenylhydrazine oxalate. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, reaction liquid is kept at strong acidity with concentrated hydrochloric acid to guarantee successful and complete reaction; in the reduction step, zinc powder-concentrated hydrochloric acid is used as a reducing agent and replaces sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, so that the reducing property is high, the yield is high, and the reaction time is shortened; impurities, such as zinc hydroxide, which are generated after reaction are convenient to remove, so that the number of product impurities is small, and the purity is high; in the salification step, leaching is carried out with acetone, so that the purity of a product is improved, and the appearance of the product is guaranteed. The preparation method is stable and reliable in process, easy to operate and high in product purity (the content measured based on high performance liquid chromatography is greater than or equal to 99.2 percent); the yield is greater than or equal to 42 percent, so that the requirement of the market for the 4-fluorophenylhydrazine oxalate can be completely met.
- -
-
Paragraph 0017; 0018; 0019; 0020; 0021-0024; 0037-0044
(2017/08/28)
-
- Preparation method for 4-fluorophenylhydrazine sulfate
-
The invention relates to a preparation method for 4-fluorophenylhydrazine sulfate. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, concentrated hydrochloric acid is adopted for maintaining a reaction liquid in strong acidity, and guaranteeing smooth and complete reaction. In the step of reduction, zinc powder-concentrated hydrochloric acid is adopted as a reducing agent for replacing sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, the reducing property is good, the yield coefficient is high, the reaction time is shortened, impurities such as zinc hydroxide generated after reaction can be removed conveniently, the product impurities are small, and the purity is high. In the step of salification, acetone is adopted for elution, the product purity is increased, and the product appearance is guaranteed. According to the preparation method, the process is stable and reliable, operation is easy, the product purity is high (the content of the 4-fluorophenylhydrazine sulfate is measured through high performance liquid chromatography and is no smaller than 99.1%), the yield coefficient is no smaller than 42%, and the market demand for the 4-fluorophenylhydrazine sulfate can be fully met.
- -
-
Paragraph 0017; 0018; 0019; 0023-0024; 0027-0034; 0037-0044
(2017/08/28)
-
- Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors
-
Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.
- Zhao, Sijia,Zhang, Yu,Zhou, Hongyang,Xi, Shuancheng,Zou, Bin,Bao, Guanglong,Wang, Limei,Wang, Jiao,Zeng, Tianfang,Gong, Ping,Zhai, Xin
-
-
- Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
-
A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.
- Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
-
-
- Synthesis of benzofuro[3,2-b] indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles
-
We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.
- Tomakinian, Terry,Guillot, Régis,Kouklovsky, Cyrille,Vincent, Guillaume
-
supporting information
p. 5443 - 5446
(2016/05/09)
-
- Indole-3-carbinol and 1,3,4-oxadiazole hybrids: Synthesis and study of anti-proliferative and anti-microbial activity
-
In the present study, molecular hybrids of indole-3-carbinol and 1,3,4-oxadiazole-2-thiols have been designed and synthesized. The thiol analogues consisted of diversely substituted benzyl and alkyl groups with different electronic properties. The structures of all the newly synthesized scaffolds and target compounds were ascertained using 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. All the final compounds were screened in vitro for their anti-proliferative and anti-microbial activity. Three compounds showed excellent anti-proliferative activity with more than 70% cell growth inhibition against three cancer cell lines, HepG2 (human liver hepatocellular carcinoma), HeLa (human cervix carcinoma), and MCF-7 (human breast carcinoma). In the anti-microbial studies, compounds with electron-withdrawing fluoro or nitro substituent displayed appreciable activity similar to that of standard drugs. Also, the final compounds are non-toxic to non-cancerous Vero cell line.
- Gokhale, Nikhila,Panathur, Naveen,Dalimba, Udayakumar,Kumsi, Manjunatha
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p. 1603 - 1613
(2015/10/20)
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- Remazol-Catalyzed Hydroperoxyarylation of Styrenes
-
A mild photocatalytic hydroperoxyarylation of styrenes has been developed, in which a novel photocatalyst, remazol brilliant blue R (RBBR), is employed at low catalytic loading (1 mol%). The operationally easy procedure uses air as the dioxygen source. Simple mono-substituted styrenes react with aryl hydrazines in moderate-to-good yields. RBBR is proposed to act as a photosensitizer for the generation of singlet oxygen.
- Chen, Ying-Ho,Lee, Ming,Lin, Yi-Zhen,Leow, Dasheng
-
supporting information
p. 1618 - 1621
(2015/08/06)
-
- Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-β-carbolines
-
Functionalized spiro-tetrahydro-β-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramolecular reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate.
- Yang, Yan-Fang,Li, Lian-Hua,He, Yu-Tao,Luo, Jian-Yi,Liang, Yong-Min
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p. 702 - 707
(2014/02/14)
-
- Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives
-
Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl) ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3- triazol-4-yl)-4,9-dihydro-3H-β-carbolines that can be transformed into β-carboline and tetrahydro-β-carboline derivatives.
- Pohodylo,Matiichuk,Obushak
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p. 275 - 279
(2014/04/17)
-
- Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition
-
In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-{1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3- yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia.
- Panathur, Naveen,Dalimba, Udayakumar,Koushik, Pulla Venkat,Alvala, Mallika,Yogeeswari, Perumal,Sriram, Dharmarajan,Kumar, Vijith
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p. 125 - 138
(2013/10/01)
-
- Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400
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An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.
- Chen, Junmin,Zhang, Yimin,Hao, Wenyan,Zhang, Rongli,Yi, Fei
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p. 613 - 617
(2013/07/25)
-
- Regioselective radical arylation of anilines with arylhydrazines
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Substituted 2-aminobiphenyls have been prepared from arylhydrazines and anilines via radical arylation reactions under simple oxidative conditions. The strong directing effect of the free and unprotonated amino functionality leads to high regioselectivities, and anilines have been shown to be significantly better aryl radical acceptors than nitrobenzenes or phenyl ethers. The methodology is also applicable to phenols, which react best as phenolates under strongly basic conditions. Finally, radical arylation reactions of anilines and anilinium salts under various conditions have for the first time demonstrated that regioselectivity can also be controlled through the rearomatization step and that the addition of an aryl radical to a substituted benzene might even be reversible.
- Jasch, Hannelore,Scheumann, Julia,Heinrich, Markus R.
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p. 10699 - 10706
(2013/02/25)
-
- Palladium-catalyzed cross-coupling of aryl chlorides and tosylates with hydrazine
-
Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl).
- Lundgren, Rylan J.,Stradiotto, Mark
-
supporting information; experimental part
p. 8686 - 8690
(2011/01/08)
-
- 4-substituted tert-butyl phenylazocarboxylates-synthetic equivalents for the para-phenyl radical cation
-
First electrophile, then radical: 4-Substituted tert-butyl phenylazocarboxylates 1 are versatile synthetic equivalents of the para-phenyl radical cation 2. The tert-butyloxycarbonylazo group enables nucleophilic substitutions to proceed under mild conditions and can later be employed for the generation of aryl radicals. Copyright
- Hoefling, Sarah B.,Bartuschat, Amelie L.,Heinrich, Markus R.
-
supporting information; experimental part
p. 9769 - 9772
(2011/02/22)
-
- Synthesis and biological activity of functionalized indole-2-carboxylates, triazino- and pyridazino-indoles
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Condensation of aryl hydrazines with ethyl pyruvate gave the respective hydrazones 4-6; Fischer indolization led to substituted-1H-indole-2-carboxylic acid ethyl esters 7-9. The Mannich reaction of these compounds with formaldehyde and morpholine yielded ethyl 3-(morpholinomethyl)-substituted-1H-indole-2- carboxylates 10-12. The 5,7-dichloro-1H-indole-2-carbohydrazide 13 was cyclized with methyl orthoformate in DMF to give 6,8-dichloro[1,2,4]triazino[4,5-a]indol- 1(2H)-one 14. Vilsmeier-Haack formylation of 7-9 gave ethyl 3-formyl- substituted-1H-indole-2-carboxylates 15-17 whose 2,2′-((5-chloro-2- (ethoxycarbonyl)-1H-indol-3-yl)methylene)bis-(sulfanediyl) diacetic acid 18 was prepared. The reaction of 15 and 16 with substituted anilines by conventional and microwave methods gave ethyl 3-(N-aryliminomethyl)-5-halo-1H-indole-2- carboxylates 19-29. In a cyclocondensation reaction of 19-25 with thiolactic acid or thioglycolic acid substituted indolylthiazolidinones 30-33 were prepared. Reaction of hydrazine hydrate with 15-17 did not give the respective hydrazones but directly led to the cyclized products substituted-3H- pyridazino[4,5-b]indol-4(5H)-ones 34-36, while a reaction with 2,4-dichlorophenylhydrazine yielded the uncyclized hydrazones. The chlorination of 35 and 36 with POCl3 gave pyridazino[ 4,5-b]indoles 39 and 40, respectively; reaction of the latter compounds with morpholine gave 4-(substituted-5H-pyridazino[4,5-b]indol-4-yl)morpholine 41 and 42. Mannich reaction of 34 with formaldehyde and N-ethylpiperazine gave 8-chloro-3-((4- ethylpiperazin-1-yl)methyl)-3H-pyridazino[ 4,5-b]indol-4(5H)-one 43. The microwave assistance of selected reactions has a profound effect on the reaction speed. The structures of the new compounds were confirmed by both analytical and spectral data. Some compounds were subjected to investigations concerning their antimicrobial, tranquilizing, and anticonvulsant activities.
- El-Gendy, Adel A.,Said, Mohamed M.,Ghareb, Nagat,Mostafa, Yasser M.,El-Ashry, El Sayed H.
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experimental part
p. 294 - 300
(2009/04/11)
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- Pyrazolones as inhibitors of 11B-hydroxysteroid dehydrogenase
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Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, type II diabetes mellitus and metabolic syndrome.
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Page/Page column 17-18
(2008/06/13)
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- Novel chemoselective reduction of aryldiazonium fluoroborates with Zn- NiCl2·6H2O-THF
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Substituted aryldiazonium fluoroborates are selectively reduced to the corresponding phenylhydrazines by using Zn-NiCl2·6H2O in THF as a reducing agent.
- Bandgar,Uppalla
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p. 714 - 715
(2007/10/03)
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- Kinetics of the Alkaline Hydrolysis of several Alkyl Phenylcarbazates
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The kinetics in 25percent (v/v) dioxane-water of the alkaline hydrolysis, followed by UV spectrometry, of several alkyl phenylcarbazates (Ar-NH-NHCOOR, with Ar = phenyl, 4-chlorophenyl, 4-fluorophenyl, 3,4-dichlorophenyl and R = methyl, ethyl, propyl, chloroethyl, trichloroethyl) are discussed.The pKa of trichloroethyl phenylcarbazate is 14.12 at 25 deg C.The pH profiles, the activation entropy of -40 cal mol-1 K-1, the kinetic solvent isotope effect, kOH-/kOD-, of 3.45, the general-base catalysis and the effect of the leaving group and of the substituent on the aromatic ring are in agreement with the involvement of a BAc2 reaction scheme.
- Safraoui, Adil,Calmon, Michelle,Calmon, Jean-Pierre
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p. 1349 - 1352
(2007/10/02)
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- Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine
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Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.
- Harden,Quinn,Scammells
-
p. 2892 - 2898
(2007/10/02)
-
- Studies in spiro heterocycles. Part 4(1): Investigation of the reactions of fluorinated 3-aroylmethylene-indol-2-ones with hydrazine and phenylhydrazine and synthesis of spiro [indole-3,3'-pyrazol]-2-ones.
-
Reactions of various 3-aroylmethylene-indol-2-ones with hydrazine and phenylhydrazine under exactly similar conditions have been carried out. The reaction with phenylhydrazine has not been investigated earlier. It was found that although the reaction with hydrazine hydrate afforded a spiro derivative viz., spiro[3H-indole-3,3'-(3H)pyrazol]-2(1H)-one, that with phenylhydrazine yielded simply a hydrazone derivative. Representative spiro compounds have been screened for antifertility activity but none was found active at a dose of 10 mg/kg in adult female rats.
- Joshi,Jain,Garg
-
-
- Isoxazolyl indolamines
-
This disclosure describes compounds of the formula STR1 wherein R1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, and R2 represents lower alkyl or STR2 where R5 represents hydrogen, fluoro, chloro, lower alkyl or lower alkoxy, and R3 and R4 each independently represent lower alkyl as defined above, and R3 and R4 together with N represent STR3 or pharmaceutically acceptable acid addition salts thereof, which are useful as anti-diabetic agents.
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-
- Pyrazol-4-acetic acid compounds
-
Pyrazol-4-acetic acid compounds, such as substituted pyrazol-4-acetic acid, its esters, amides, nitriles and their pharamaceutically acceptable salts and method for the preparation of these compounds are disclosed. The novel compounds are useful analgesics, anti-inflammatory, and antipyretics.
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-
- (Nitrofuryl)pyrazoles, their synthesis and use, and compositions containing them
-
3-(5-Nitro-2-furyl)pyrazoles unsubstituted in the 5-position and 5-(5-nitro-2-furyl)pyrazoles unsubstituted in the 3-position are antimicrobials and disinfectants. The compounds are structurally represented by one of the formulae: STR1 wherein A is --CHO, --CN, --COOH, a protected or derived aldehyde group or a protected or derived carboxylic acid group; B is 5-nitro-2-furyl; R1 is --H, substituted or unsubstituted hydrocarbyl (saturated or unsaturated; acyclic, alicyclic or aromatic; or araliphatic); substituted or unsubstituted (cycloaliphatic or aromatic) heterocyclic or acyl (carboxylic or carbonic acid); R2 is --H; and n is a positive whole number of at most 2.
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- Process for producing 3-anilino-5-pyrazolones
-
A process for producing a 3-anilino-5-pyrazolone which comprises reacting a β-anilino-β-alkoxy-acrylate with a hydrazine in the presence of a compound having a pKa of about 8 up to about 14.
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