- Recycling and reuse technology for preparing triphenylchloromethane
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The invention provides a recycling and reuse technology for preparing triphenylchloromethane. The technology comprises the following steps that hydrochloric acid or a mixture of the hydrochloric acidand Lewis acid is added into a solvent of triphenylcarbinol, stirring is conducted at a certain temperature, after a reaction is finished, separation is conducted, or after separation, recrystallization is further conducted, and the triphenylchloromethane is obtained after drying, wherein the reaction equation is shown in the description. The reuse technology is a recycling and reuse technology which is wide in raw material source, low in price and simple in production process operation and causes little pollution, and the technology is very suitable for commercialized production.
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Paragraph 0067-0074
(2019/10/01)
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- Method for synthesizing high-purity sartan side chain TTBB
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The invention discloses a method for synthesizing high-purity sartan side chain TTBB. The method comprises the following steps: taking 4-methyl-2-cyanobiphenyl as a starting material; under a catalytic action of lewis acid triethylamine hydrochloride, carrying out cyclization reaction on the 4-methyl-2-cyanobiphenyl and sodium azide to generate a 5-[2-(4'-methyldiphenyl)]tetrazole compound; reacting the 5-[2-(4'-methyldiphenyl)] tetrazole compound with triphenylchloromethane under an alkaline condition to generate an N-(triphenylmethyl)-5-(4'-methylbiphenyl-2-yl)tetrazole compound; reacting togenerate a mixture of a compound TTBB and a compound Br-TTBB under the action of bromine-containing substances; promoting the compound Br-TTBB to be converted into the compound TTBB under the actionof diethyl phosphite by the mixture, thus finally obtaining the high-purity sartan side chain TTBB. The synthetic process disclosed by the invention has the advantages of better economical property, environment friendliness, high efficiency, simplicity and convenience; the mode of improving the purity of a target product through recrystallization for multiple times by adopting a conventional method is avoided.
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Paragraph 0020; 0040-0042
(2018/06/15)
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- Method of ortho-arylation of special functional group on palladium/carbon catalytic benzene ring
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The invention discloses a method of ortho-arylation of a special functional group on a palladium/carbon catalytic benzene ring. The invention discloses a method of ortho-iodination of a special functional group on the palladium/carbon catalytic benzene ring. The method comprises the following steps: dissolving an aromatic ring with a substrate containing the special functional group, palladium/carbon as a catalyst, a hypervalent iodine agent and an alkaline substance into a solvent, carrying out reaction at the temperature of 80-120 DEG C for 5-12h, and after the reaction is completed, carrying out post-treatment on a reaction solution to obtain a substituted biphenyl product. The method has the advantages that the used method route cannot enable a great quantity of industrial waste water to be generated and is smaller in environmental pollution; a product obtained by reaction is high in yield and good in selectivity; and the used catalyst can be recycled and reused and has a potential industrial application value.
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Paragraph 0029; 0030; 0031
(2017/07/14)
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- Bacterial Peptide Deformylase Inhibition of Tetrazole-Substituted Biaryl Acid Analogs: Synthesis, Biological Evaluations, and Molecular Docking Study
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The synthesis and screening of tetrazole-substituted biaryl acid analogs 7a–l as bacterial peptide deformylase (PDF) enzyme inhibitors is reported. The compounds 7e (IC50 value = 5.50 μM) and 7g (IC50 value = 7.25 μM) showed good PDF inhibition activity. The compounds 7e (MIC range = 10.75–11.66 μg/mL) and 7g (MIC range = 8.91–12.83 μg/mL) also showed potent antibacterial activity when compared with the standard ciprofloxacin (MIC range = 25–50 μg/mL). Thus, the active derivatives were not only potent PDF enzyme inhibitors but also efficient antibacterial agents. In order to gain more insight into the binding mode of the compounds with the PDF enzyme, the most active compounds 7e and 7g, the moderately active compound 7k, and the least active compound 7h were docked against the PDF enzyme of Escherichia coli. The docking study of the most active compounds 7e and 7g against the PDF enzyme exhibited good binding properties. Hence, we believe our synthesized compounds 7a–l could serve as reservoir for bacterial PDF inhibitor development.
- Khan, Firoz A. Kalam,Patil, Rajendra H.,Patil, Manjiri,Arote, Rohidas,Shinde, Devanand B.,Sangshetti, Jaiprakash N.
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p. 934 - 943
(2016/12/09)
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- Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles
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A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring.
- Behloul, Cherif,Bouchelouche, Kenza,Hadji, Yasmine,Benseghir, Saadia,Guijarro, David,Nájera, Carmen,Yus, Miguel
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supporting information
p. 2455 - 2460
(2016/07/28)
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- 1,(3,)5-substituted imidazoles, useful in the treatment of hypertension and methods for their preparation
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The present invention provides novel 1,5 and 1,3,5-substituted imidazole compounds in hydrophilic or lipophilic form, which are useful as angiotensin II ATI receptor antagonists suitable for transdermal delivery. The invention also provides pharmaceutical compositions containing such compounds, processes and intermediates for preparing compounds and their use in methods of treating hypertension and cardiovascular diseases.
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Paragraph 0219
(2016/03/04)
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- Indium-Mediated Cleavage of the Trityl Group from Protected 1 H -Tetrazoles
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On treatment with indium metal in MeOH-THF, trityl groups undergo reductive removal from 1H-protected tetrazoles (including aliphatic, aromatic, and heteroaromatic substituents), affording the corresponding free tetrazoles in excellent yields, without any decomposition of the tetrazole ring or reduction of any other group.
- Behloul, Cherif,Bouchelouche, Kenza,Guijarro, David,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
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supporting information
p. 2399 - 2402
(2015/10/19)
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- Synthesis of new biphenyl-substituted quinoline derivatives, preliminary screening and docking studies
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New quinoline derivatives containing biphenyl ring were synthesized and characterized by IR, 1H NMR and mass spectral studies. The synthesized compounds were screened for antimicrobial, anthelmintic activities as well as free radical scavenging property against the DPPH radical. The minimum inhibition concentration values showed promising inhibiting activity and are potent biological agents. The compounds showed minimum binding energy towards ?-tubulin. The compounds 11a, 11c, 13c and 13d have good affinity towards the active pocket and may be considered as a good inhibitor of β-tubulin. Indian Academy of Sciences.
- Shashikumar, Nellisara D.,Krishnamurthy, Ganganaika,Bhojyanaik, Halehatti S.,Lokesh, Mayasandra R.,Jithendrakumara, Kaginalli S.
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p. 205 - 212
(2014/04/03)
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- Synthesis of new biphenyl-substituted quinoline derivatives, preliminary screening and docking studies
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New quinoline derivatives containing biphenyl ring were synthesized and characterized by IR, 1H NMR and mass spectral studies. The synthesized compounds were screened for antimicrobial, anthelmintic activities as well as free radical scavenging property against the DPPH radical. The minimum inhibition concentration values showed promising inhibiting activity and are potent biological agents. The compounds showed minimum binding energy towards β-tubulin. The compounds 11a, 11c, 13c and 13d have good affinity towards the active pocket and may be considered as a good inhibitor of β-tubulin.
- Shashikumar, Nellisara D,Krishnamurthy, Ganganaika,BhojyaNaik, Halehatti S,Lokesh, Mayasandra R,Jithendrakumara, Kaginalli S
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p. 205 - 212
(2016/03/01)
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- Detritylation of protected tetrazoles by naphthalene-catalyzed lithiation
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Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl-tetrazole and trityl-amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions. Georg Thieme Verlag Stuttgart, New York.
- Behloul, Cherif,Bouchelouche, Kenza,Guijarro, David,Nájera, Carmen,Yus, Miguel
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p. 2065 - 2070
(2014/08/05)
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- N-ARYLYLMETHYLINDAZOLE MODULATORS OF PPARG
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The invention provides molecular entities that bind with high affinity to PPARG (PPARy), inhibit cdJk5-mediated phosphorylation of PP ARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes or obesity. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.
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- Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors
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The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7.
- Sánchez, Ana I.,Martínez-Barrasa, Valentín,Burgos, Carolina,Vaquero, Juan J.,Alvarez-Builla, Julio,Terricabras, Emma,Segarra, Víctor
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p. 2370 - 2378
(2013/05/09)
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- An efficient synthesis, X-ray and spectral characterization of biphenyl derivatives
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Derivatives of 1,3-thiazolidin-2,4-dione appended to biphenyl ring viz., 7-9, 16-18 were prepared. The newly synthesized compounds were confirmed by IR, NMR (1H and 13(C) MS and elemental analyses. Single crystal X-ray diffraction study was carried out for one of the final compounds 9. Indian Academy of Sciences.
- Kamble, Ravindra R.,Biradar, Dharesh B.,Meti, Gangadhar Y.,Taj, Tasneem,Gireesh, Tegginamath,Khazi, Imthiyaz Ahmed M.,Vaidyanathan, Sundar T.,Mohandoss, Raju,Sridhar, Balasubramanian,Parthasarathi, Viraraghav
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experimental part
p. 393 - 401
(2012/04/04)
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- Synthesis and characterization of 4′-bromomethyl-2-(N-trityl-1H- tetrazol-5-yl) biphenyl
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Biphenyl tetrazole ring is an important component of the Sartan family of novel drugs. 4′-Bromomethyl-2-(N-trityl-1H-tetrazol-5-yl)biphenyl was synthesized in this article from 4′-methyl-2-cyano-biphenyl through three steps. 4′-Methyl-2-cyano-biphenyl was reacted with azide ions with the help of ammonium chloride as catalyst in an autoclave with high conversion to afford the tetrazole compounds in 70.6% yield. After being protected by the trityl group with 92.6% yield, 4′-methyl-2-(N-trityl-1H-tetrazol-5-yl) biphenyl was brominated with N-bromosuccinimide (NBS) in cyclohexane with 2,2′-azo-isobutyronitrile (AIBN) acting as an initiator to provide the title compound in 83.8% yield. Copyright Taylor & Francis Group, LLC.
- Wang, Guo-Xi,Sun, Bao-Ping,Ru, Zong-Ling
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p. 3577 - 3581
(2008/12/23)
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- Nonpeptide angiotensin II receptor antagonists: Synthesis and biological activity of 1H-Imidazo and 1H-[1,2,3]-Triazolo fused derivatives
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A series of 1H-Imidazo and 1H-[1,2,3]-Triazolo fused derivatives have been obtained and tested as non peptide AII receptor antagonists. Modification of the classical biphenyl moiety to a 4-arylthienyl fragment afforded interesting activities.
- Delgado,Pastor,Garcia-Navio,Vaquero,Alvarez-Builla,Sunkel,De Casa-Juana,Priego,Santos,Statkow,Straumann
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p. 147 - 155
(2007/10/03)
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- 4-(1H-PYRROL-1-YL)IMIDAZOLES WITH ANGIOTENSIN II ANTAGONIST ACTIVITY
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Novel substituted 4-(1-H-pyrrol-1-yl)imidazoles are disclosed as well as methods of preparing them, pharmaceutical compositions containing them, and methods of using them. Novel intermediates useful in the preparation of the compounds of the invention are also disclosed and synthetic methods for preparing the novel intermediates. The compounds are useful as antagonists of angiotensin II and thus are useful in the control of hypertension, hyperaldosteronism, congestive heart failure, glaucoma, vascular smooth muscle proliferation associated with atherosclerosis, and with postsurgical vascular restenosis.
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- N-SUBSTITUTED HETEROCYCLIC DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS IN WHICH THEY ARE PRESENT
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The invention relates to N-substituted heterocyclic derivatives and its salts. These derivatives have the formula (I) in which the substituents are as defined in the specification. Application: Angiotensin II antagonists
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- Fused aryl substituted imidazole angiotensin II receptor inhibitors
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Substituted imidazoles such as STR1 which are useful as angiotensin II receptor inhibitors. These compounds have activity in treating hypertension and congestive heart failure.
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- 4-(1H-PYRROL-1-YL) IMIDAZOLES WITH ANGIOTENSION II ANTAGONIST ACTIVITY
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Novel substituted 4-(1-H-pyrrol-1-yl)imidazoles are disclosed as well as methods of preparing them, pharmaceutical compositions containing them, and methods of using them. Novel intermediates useful in the preparation of the compounds of the invention are also disclosed and synthetic methods for preparing the novel intermediates. The compounds are useful as antagonists of angiotensin II and thus are useful in the control of hypertension, hyperaldosteronism, congestive heart failure, glaucoma, vascular smooth muscle proliferation associated with atherosclerosis, and with postsurgical vascular restenosis.
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- ANGIOTENSIN II RECEPTOR BLOCKING IMIDAZOLES
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Substituted imidazoles such as STR1 are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.
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- Treatment of congestive heart failure with angiotensin 11 receptor blocking imidazoles
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Substituted imidazoles such as STR1 are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.
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- Three Synthetic Routes to a Sterically Hindered Tetrazole. A New One-Step Mild Conversion of an Amide into a Tetrazole
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5--1H-tetrazole (6), which contains a sterically hindered o-tetrazole group, was synthesized by three different routes, one of them employing a new tetrazole synthesis.The first involved the reaction of trialkyltin azides with 4'-methyl-1,1'-biphenyl-2-carbonitrile (3).The resultant trimethyltin-tetrazole adduct could be hydrolyzed with acid to yield biphenylyltetrazole 6.The tri-n-butyltin-tetrazole adduct, however, was transformed into the corresponding N-trityl-protected tetrazole 5 to permit removal of the organic soluble tri-n-butyltin byproducts.The trityl group also permits 5 to be brominated at the benzylic position and then alkylated by imidazole derivatives.Subsequent acid hydrolysis of the trityl protecting group of 5 yielded biphenylyltetrazole 6.The second synthesis involved the nitrosation of an N-(2-cyanoethyl)-protected biphenylamidrazone 10 using N2O4 (g) to yield N-(2-cyanoethyl)-protected tetrazole 12.Aqueous base removes the cyanoethyl protecting group to yield biphenylyltetrazole 6.The third method involves the novel transformation of an N-(2-cyanoethyl)-substituted amide into the corresponding N-(2-cyanoethyl)-protected tetrazole in one step using triphenylphosphine, diethyl azodicarboxylate (DEAD), and azidotrimethylsilane.Subsequent base hydrolysis of the cyanoethyl group yielded 6 as before.Examples are also provided of the application of this new reaction to other N-(2-cyanoethyl)-protected carboxamides.
- Duncia, John V.,Pierce, Michael E.,Santella, Joseph B.
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p. 2395 - 2400
(2007/10/02)
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