- N -Chlorinative Ring Contraction of 1,4-Dimethoxyphthalazines via a Bicyclization/Ring-Opening Mechanism
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An unprecedented N -chlorinative ring contraction of 1,2-diazines was discovered and investigated with an electrophilic chlorinating reagent, trichloroisocyanuric acid (TCICA). Through optimization and mechanistic analysis, the assisting role of n -Bu 4NCl as an exogenous nucleophile was identified, and the optimized reaction conditions were applied to a range of 1,4-dimethoxyphthalazine derivatives. Also, an improvement of overall efficiency was demonstrated by the use of a labile O -silyl group. A bicyclization/ring-opening mechanism, inspired by the Favorskii rearrangement, was proposed and supported by the DFT calculations. Furthermore, the efforts on scope expansion as well as the evaluation of other electrophilic promoters revealed that the newly developed ring contraction reactivity is a unique characteristic of 1,4-dimethoxyphthalazine scaffold and TCICA.
- Im, Jeong Kyun,Jeong, Ilju,Yang, Byeongdo,Moon, Hyeon,Choi, Jun-Ho,Chung, Won-Jin
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p. 1760 - 1770
(2020/12/30)
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- Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea
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N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.
- Liu, Luxiao,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
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p. 1351 - 1357
(2019/11/19)
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- Compound for inhibiting IDO and application of compound
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The invention discloses a compound for inhibiting IDO and application of the compound, in particular to application of a compound shown in formula I, or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, or a solvate thereof, or a prod
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Paragraph 0172; 0174-0176
(2019/12/25)
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- PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
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A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
- Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
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p. 1180 - 1185
(2019/01/26)
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- Novel n-channel organic semiconductor based on pyrene-phenazine fused monoimide and bisimides
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Large π-conjugated pyrene-phenazine monoimide and bisimides were synthesized by imine condensation reaction. These imides form well ordered 1D nanotapes upon self-assembly in solution. Electrochemical and electric conductivity measurement reveal it can be served as an n-channel semiconductor with large charge carrier mobility up to 4.1 cm2 V?1 s?1. Both alkylated imides are highly luminescent, and can be quenched via protonization using trifluoroacetic acid, which could be served as potential colorimetric acid sensors.
- Song, Xiaoyu,Zhao, Jing,Zhang, Wandong,Chen, Long
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p. 331 - 335
(2017/10/17)
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- Synthesis method of phthalimide and phenyl ring-substituted phthalimide derivative
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The invention provides a synthesis method of phthalimide and a phenyl ring-substituted phthalimide derivative. The synthesis method comprises that aromatic ketone and ammonia gas or an ammonia gas precursor as substrates and air or oxygen as an oxygen source undergo a reaction under catalyst action and liquid phase conditions to produce phthalimide and a phenyl ring-substituted phthalimide derivative. The synthesis method is mild, realizes high oxidation efficiency and a high product yield, utilizes oxygen or air as an oxygen source, is economic and eco-friendly and has a good application prospect.
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Paragraph 0013; 0017; 0018; 0020; 0024; 0028
(2017/08/25)
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- Isoindol - 1, 3 - dione compound and its preparation method and application (by machine translation)
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The invention discloses a isoindole - 1, 3 - dione compound and its preparation method and application. The general formula (I) has the structure shown. The invention of the isoindole - 1, 3 - diones to LNCap cells with cell inhibitory activity, can be used for preparing anti-tumor drug. (by machine translation)
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- ALLOSTERIC PROTEIN KINASE MODULATORS
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The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.
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Page/Page column 46
(2012/03/10)
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- ALLOSTERIC PROTEIN KINASE MODULATORS
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The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.
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Page/Page column 95
(2010/04/30)
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- Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them
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The present invention relates to the novel isoindolone derivatives of the formula I in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.
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Page/Page column 30
(2008/06/13)
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- N- ((3-OXO2, 3-DIHYDRO-1H-ISOINDOL-1-YL) ACETYL) GUANIDINE DERIVATIVES AS NHE-1 INHIBITORS FOR THE TREATMENT OF INFARCTION AND ANGINA PECTORIS
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Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them. The present invention relates to the novel isoindolone derivatives of the Formula (I), in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.
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- Imidation of cyclic carboxylic anhydrides under microwave irradiation
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Efficient and facile conversion of cyclic carboxylic anhydrides to corresponding imides with formamide under microwave irradiation is described.
- Peng,Song,Qian
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p. 1927 - 1931
(2007/10/03)
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- Inhibitors of microsomal triglyceride transfer protein and method
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Compounds are provided which inhibit microsomal triglyceride transfer protein and thus are useful for lowering serum lipids and treating atherosclerosis and related diseases. The compounds have the structure STR1 wherein R1 to R7, Q, X and Y are as defined herein.
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- Nucleic acids encoding microsomal trigyceride transfer protein
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Nucleic acid sequences, particularly DNA sequences, coding for all or part of the high molecular weight subunit of microsomal triglyceride transfer protein, expression vectors containing the DNA sequences, host cells containing the expression vectors, and methods utilizing these materials. The invention also concerns polypeptide molecules comprising all or part of the high molecular weight subunit of microsomal triglyceride transfer protein, and methods for producing these polypeptide molecules. The invention additionally concerns novel methods for preventing, stabilizing or causing regression of atherosclerosis and therapeutic agents having such activity. The invention concerns further novel methods for lowering serum liquid levels and therapeutic agents having such activity.
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- Synthesis, Saludiuretic, and Antihypertensive Activity of 6,7-Disubstituted 1(2H)- and 3,4-Dihydro-1(2H)-phthalazinones
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The synthesis of the isomeric series 6-chloro-7-sulfamoyl-and 7-chloro-6-sulfamoyl-1(2H)-phthalazinones (1 and 2) and 6-chloro-7-sulfamoyl- and 7-chloro-6-sulfamoyl-3,4-dihydro-1(2H)-phthalazinones (3 and 4), combining structural features characteristic to furosemide and hydralazine, is described, the mechanism of the formation of 1 and 2 is discussed, and their structure-activities relationships are studied.Preliminary screening in the rat shows that series 1 and 3 exhibit diuretic and saluretic activity similar to that of chlorothiazide with, however, Na+/K+ ratios more favorable than chlorothiazide and furosemide.The compounds of series 2 and 4 are practically inactive.All four series show initial antihypertensive activity lower than that of hydralazine.However, compounds 1a, 1c, and 4a show a higher activity at 8 and/ or 24 h after administration and thus may offer a unique combination of a "loop" diuresis with direct long-acting peripheral vasodilating effects.
- Cherkez, S.,Herzig, J.,Yellin, H.
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p. 947 - 959
(2007/10/02)
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- Kinetic and equilibrium in the ammonolysis of substituted phthalimides
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Kinetic studies are reported for the base hydrolysis to phthalamic acid anions (H) and ammonolysis to phthalamides (A) for seven phthalimides (P): 1, unsubstituted; 2, 4-NO2; 3, 4-Cl; 4, 4-tBu; 5, 3-NO2; 6, 3-Me; 7, 3-Me3Si.The hydrolysis kinetics require two mechanisms, one which is first order in neutral imide and first order in hydroxide ion, and a second, which is important only in quite concentrated NaOH, which is first order in neutral phthalimide and second order in hydroxide ion.Ammonolysis kinetics for 1-5 revealed the rate law: Rate = kN ->.A mechanism is proposed with rate-determining breakdown of the anionic form of the tetrahedral intermediate derived by addition of NH3 to the phthalimide.The ammonolysis is reversible.The phthalamide hydrolyzes to the phthalamic acid via cyclization to an intermediate phthalimide, which is detected in concentrated base where its formation from phthalamide is more rapid than its subsequent hydrolysis.Rate constants for the cyclization follow the rate law: Rate = kcyc ->.This reaction is the microscopic reverse of the ammonolysis, and the ratio kN/kcyc provides the equilibrium constant Keq for the reaction P + NH3 = A.Values for 1-5 lie in the range 2 x 102 - 4 x 103.With 3-methylphthalimide, kinetics in aqueous ammonia do not obey a first-order relationship, but they could be analyzed by a scheme whereby the phthalimide is converted reversibly to the phthalamide and simultaneously undergoes an irreversible hydrolysis.The value of Keq in the system is 1.8.With 3-trimethylsilylphthalimide the value of Keq is further reduced to 0.01.The ammonolysis reaction does occur more quickly than hydrolysis but the equilibrium is so unfavorable that even in concentrated ammonia only a small amount of the phthalamide is ever formed.
- McClelland, Robert A.,Seaman, N. Esther,Duff, James M.,Branston, R. E.
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p. 121 - 128
(2007/10/02)
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- Photochemical Additions of Alkenes to Phthalimides. Mechanistic Investigations on the Stereochemistry of Alkene Additions and the Effect of Aryl Substituents on the Regiochemistry of Alkene Additions
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The mechanism of the photochemical addition of alkenes to phthalimides was investigated by determining the stereochemistry of the addition and the effect of aryl substituents on the regiochemistry.Intra- and intermolecular examples were examined.The stereochemistry of the addition of cis- and trans-2-butene to N-methylphthalimide to give 2,3,4-trimethyl-2-benzazepine-1,5-dione was studied.It was found that both alkenes added stereospecifically, each giving the corresponding cis- or trans-2,3,4-trimethyl-2-benzazepine-1,5-dione with >95percent stereospecificity.The mechanistic implication of this result is either that the photochemical addition is a concerted (2 + 2) addition or that any intermediate biradical closes faster than rotation around the C-C bond which would result in loss of stereochemistry.A second approach to this problem employed the directive effects of aryl substituents.The proposed biradical intermediate is similar in structure to the phthalimide radical anion.The directive effects of aryl substituents have been experimentally determined in this system and are consistent with theoretical predictions.Theoretical predictions for aryl-substituent directive effects in the alternative concerted (2 + 2) process are opposite to those for the biradical case, which predicts that donors will direct meta and acceptors para.Irradiation of 4-methoxy- and 4-carbomethoxy-N-methylphthalimide in the presence of 1-hexene afforded the benzazepinedione addition products that resulted from addition to the para and meta C(O)-N bonds, respectively.These results are entirely consistent with a concerted process.
- Mazzocchi, P. H.,Wilson, P.,Khachik, F.,Klingler, L.,Minamikawa, S.
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p. 2981 - 2989
(2007/10/02)
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