- Hydroxybenzoyl Chlorides in the Synthesis of Conjugates with Biologically Active Dipeptides
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Abstract: Conjugates of hydroxy- and acetoxybenzoic acids with dipeptides based on 4-aminobutanoic acid and glycine were synthesized through hydroxy(acetoxy)benzoyl chlorides and 4-[hydroxy(acetoxy)benzoyl-amino]butanoyl chlorides as intermediate products. Acyl chlorides were prepared by treatment of the corre-sponding acids with oxalyl chloride in the presence of dimethylformamide at a ratio of 1:1.1:0.07 in boiling benzene. The target N-[hydroxy(acetoxy)benzoyl] derivatives of dipeptides were obtained with high yields, and no further purification of the products was necessary. The synthesized compounds were evaluated as potential neuroprotective agents.
- Brel, A. K.,Budaeva, Yu. N.,Lisina, S. V.
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p. 540 - 544
(2021/06/02)
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- Total Synthesis and Biological Evaluation of Tiancimycins A and B, Yangpumicin A, and Related Anthraquinone-Fused Enediyne Antitumor Antibiotics
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The family of anthraquinone-fused enediyne antitumor antibiotics was established by the discovery of dynemicin A and deoxy-dynemicin A. It was then expanded, first by the isolation of uncialamycin, and then by the addition to the family of tiancimycins A-
- Aujay, Monette,Das, Dipendu,Gavrilyuk, Julia,Hammond, Mikhail,Lu, Yong,Lyssikatos, Joseph,Nicolaou, K. C.,Pitsinos, Emmanuel N.,Rout, Subhrajit,Sandoval, Joseph,Schammel, Alexander
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- Discovery of novel phenoxybenzamide analogues as Raf/HDAC dual inhibitors
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Histone deacetylase (HDAC)inhibitors as an important epigenetic therapeutic strategy affect signaling networks and act synergistically with kinase inhibitors for the treatment of cancer. Herein we presented a series of novel phenoxybenzamide analogues with inhibition of Raf and HDAC. Among them, compound 10e showed potent antiproliferative activities against Hepg2 and MDA-MB-468 in cellular assays. This work may lay the foundation for developing novel dual Raf/HDAC inhibitors as potential anticancer therapeutics.
- Geng, Aixin,Cui, Hao,Zhang, Liyuan,Chen, Xin,Li, Hongmei,Lu, Tao,Zhu, Yong
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supporting information
p. 1605 - 1608
(2019/05/02)
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- Uracil Hydroxybenzamides as Potential Antidiabetic Prodrugs
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A series of N1, N3-bis-hydroxybenzoyl, -acetoxybenzoyl, and -methoxybenzoyl uracil derivatives were synthesized. All compounds were screened for the ability to rupture protein cross links and antiglycating, chelating, and antiaggregant properties, which are most significant for pharmacological treatment of thrombosis and angio-, nephro-, encephalo-, and cardiopathies. 1,3-bis-(4-Methoxybenzoyl)pyrimidine-2,4(1H,3H)-dione was a promising antidiabetic agent with all studied activities.
- Brel’,Spasov,Lisina,Popov,Kucheryavenko,Litvinov,Salaznikova,Rashchenko
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p. 511 - 515
(2019/11/22)
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- A synthesis method of benzaldehyde (by machine translation)
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The invention provides a synthesis method of benzaldehyde, the method comprises: (1) the hydroxy benzoic acid as the raw material, N, N - dimethyl formamide or N, N - dimethyl acetamide as catalyst, in the presence of acyl, to carry out the following formula 1 shown between the acyl chloride reaction in order to produce hydroxy benzoyl chloride; and (2) in the presence of hydrogen, in the presence of a catalyst, in the step (1) the resulting hydroxy benzoyl chloride of the following carried out 2 is shown between the hydrogenation reduction reaction of benzaldehyde. According to the method of the present invention mild condition, few steps, synthetic high yield, production process has no waste water, compared with the traditional method, the advantages of environmental protection, energy-saving high-efficiency, small equipment footprint, the product quality is in quality. [Formula 1] [Formula 2] (by machine translation)
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Paragraph 0028; 0029-0030; 0035-0036; 0041-0042; 0047-0132
(2018/09/21)
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- New preparation method of 3-hydroxybenzoyl chloride
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The invention relates to a new preparation method of 3-hydroxybenzoyl chloride, belonging to the technical field of medical technology. The invention relates to a more advanced new preparation methodof the 3-hydroxybenzoyl chloride. In order to solve the
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Paragraph 0009; 0010
(2018/11/04)
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- 3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus
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The human rhinovirus (hRV) is the causative agent of the common cold that often aggravates respiratory complications in patients with asthma or chronic obstructive pulmonary disease. The high rate of mutations and variety of serotypes are limiting the development of anti-hRV drugs, which emphasizes the need for the discovery of novel lead compounds. Previously, we identified antiviral compound 1 that we used here as the starting material for developing a novel compound series with high efficacy against hRV-A and -B. Improved metabolic stability was achieved by substituting an ester moiety with a 1,2,4-oxadiazole group. Specifically, compound 3k exhibited a high efficacy against hRV-B14, hRV-A21, and hRV-A71, with EC50 values of 66.0, 22.0, and 3.7 nM, respectively, and a relevant hepatic stability (59.6 and 40.7% compound remaining after 30 min in rat and human liver microsomes, respectively). An in vivo study demonstrated that 3k possessed a desirable pharmacokinetic profile with low systemic clearance (0.158 L·h-1·kg-1) and modest oral bioavailability (27.8%). Hence, 3k appears to be an interesting candidate for the development of antiviral lead compounds.
- Kim, Jinwoo,Shin, Jin Soo,Ahn, Sunjoo,Han, Soo Bong,Jung, Young-Sik
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supporting information
p. 667 - 672
(2018/05/14)
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- M-hydroxy acetophenone preparation method
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The invention discloses an m-hydroxy acetophenone preparation method which includes the steps: performing chlorination, dissolving m-hydroxybenzoic acid in methylbenzene, adding 4-dimethylamino pyridine serving as a catalyst, adding acyl thionyl chloride for chlorination to obtain m-hydroxybenzoic acid acyl chloride, and then removing the acyl thionyl chloride by concentration and evaporation to obtain m-hydroxybenzoic acid acyl chloride-methylbenzene solution; dissolving dimethyl malonate sodium salt in methylbenzene to obtain dimethyl malonate sodium salt-methylbenzene solution, dripping them-hydroxybenzoic acid acyl chloride-methylbenzene solution obtained in the step (1) into the dimethyl malonate sodium salt-methylbenzene solution, and then performing reflux reaction for 3-5 hours atthe reaction temperature of 50-80 DEG C to obtain a product A; adding the obtained product A into hydrochloric acid solution, and performing hydrolysis reaction to obtain m-hydroxy acetophenone. Thepreparation method is simple in process, small in wastewater discharge amount, low in cost and high in yield and final product purity.
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Paragraph 0030; 0031; 0032; 0033; 0034; 0035; 0036-0058
(2018/10/26)
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- Evaluation of N-Hydroxy-, N-Metoxy-, and N-Acetoxybenzoyl-Substituted Derivatives of Thymine and Uracil as New Substances for Prevention and Treatment of Long-Term Complications of Diabetes Mellitus
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New uracil and thymine derivatives, N1-,N3- and N1,N3-(RO-benzoyl)-(1H,3H)-pyrimidine- 2,4-diones, were synthesized (RO- is hydroxy, acetoxy- or methoxy-group). The compounds were studied in a complex of in vitro tests for the ability to inhibit the development of long-term complications of diabetes. Their ability to cleave cross-links of proteins has been evaluated. The most significant ways of pharmacological correction of thrombosis, angio-, nephro-, encephalo-, and cardiopathy, antiglycation, chelating, and antiplatelet activities, have been established. The most active compound in terms of antiplatelet action, N1- hydroxybenzoyluracil, exceeded acetylsalicylic acid by ~44%. In terms of their ability to chelate copper (II) cations, all compounds (with the exception of 1,3-bis(3-hydroxybenzoyl)-(1H,3H)-pyrimidine-2,4-dione that was not not studied in this test) showed the activity, whose IC50 fell in the range between that for pioglitazone (44.1 μM) and pyridoxamine (136.7 μM) comparison drugs. The best antiglycation effect at the 1 mM concentration was observed for N1,N3-bismethoxy- and N1,N3-bisacetoxybenzoyl derivatives of thymine. The maximum activity to cleave cross-links of proteins (C = 1 mM), comparable to that of alagebrium, was established for 1,3-bis(4-methoxybenzoyl)uracil, for which also high rates of other estimated activities were noted. Thus, the N1-,N3- and N1,N3-(RO-benzoyl) derivatives of uracil and thymine are promising basiсs for creating drugs that suppress the development of long-term complications of diabetes.
- Spasov,Brel,Litvinov,Lisina,Kucheryavenko,Budaeva, Yu. N.,Salaznikova,Rashchenko,Shamshina,Batrakov,Ivanov
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p. 769 - 777
(2019/02/26)
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- Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
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A catalytic, versatile and atom-economical C?H functionalization process that provides a wide variety of cyclic systems featuring methyl-substituted quaternary stereocenters is described. The method relies on the use of a cationic IrI–bisphosph
- Fernández, David F.,Gulías, Moisés,Mascare?as, José L.,López, Fernando
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supporting information
p. 9541 - 9545
(2017/08/01)
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- Synthesis and Biological Evaluation of Novel FtsZ-targeted 3-arylalkoxy-2,6-difluorobenzamides as Potential Antimicrobial Agents
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Novel series of 3-O-arylalkylbenzamide and 3-O-arylalkyl-2,6-difluorobenzamide derivatives were synthesized and evaluated for their on-target activity and antibacterial activity. The results indicated that the 3-O-arylalkyl-2,6-difluorobenzamide derivativ
- Qiang, Shengsheng,Wang, Changde,Venter, Henrietta,Li, Xin,Wang, Yi,Guo, Liwei,Ma, Ruixin,Ma, Shutao
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p. 257 - 264
(2016/02/10)
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- Diaryl-1,2,4-oxadiazole antioxidants: Synthesis and properties of inhibiting the oxidation of DNA and scavenging radicals
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Six 1,2,4-oxadiazole derivatives were prepared in order to compare their abilities to protect DNA against radical-mediated oxidation and to scavenge radicals. These derivatives had a structure based on disubstituted 1,2,4-oxadiazole, in which a vanillin group (A ring) and a substituted benzene group (B ring) were the substituents. The functional group at B ring was assigned as ortho- or meta-hydroxylbenzene group, ortho-chlorobenzene group, no group contained, and pyridine group or vanillin group at B ring. It was found that the compound with two vanillin groups attaching to oxadiazole can trap 2.05 radicals in protecting DNA against 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation, and the compound with an ortho-hydroxylbenzene group at B ring can trap 1.78 radicals. The compound with an ortho-chlorobenzene group at B ring exhibited the highest ability to inhibit ·OH-induced oxidation of DNA, while the compound with a meta-hydroxylbenzene group at B ring inhibited Cu2+/glutathione (GSH)-induced oxidation of DNA efficiently. The ortho- and para-hydroxylbenzene groups at B ring made the compounds possess the highest rate constant (k) in scavenging 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.) and 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH). Therefore, only a few hydroxyl groups can markedly enhance the activity of the core-branched antioxidant, which may be a novel structural feature in designing antioxidant.
- Zhao, Chao,Liu, Zai-Qun
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p. 842 - 849
(2013/04/24)
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- Synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies of N2-acyl isonicotinic acid hydrazide derivatives
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A series of N2-acyl isonicotinic acid hydrazides (1-17) was synthesized and tested for its in vitro antimycobacterial activity against Mycobacterium tuberculosis and the results indicated that the compound, isonicotinic acid N′- tetradecanoyl-hydrazide (12) was more active than the reference compound isoniazid. The results of antimicrobial activity of the synthesized compounds against S. aureus, B. subtilis, E. coli, C. albicans and A. niger indicated that compounds with dichloro, hydroxyl, tri-iodo and N 2 -tetradecanoyl substituent were the most active ones. The antiviral activity studies depicted that none of the tested compounds were active against DNA or RNA viruses. The multi-target QSAR model was found to be effective in describing the antimicrobial activity of N2-acyl isonicotinic acid hydrazides.
- Judge, Vikramjeet,Narasimhan, Balasubramanian,Ahuja, Munish,Sriram, Dharmarajan,Yogeeswari, Perumal,De Clercq, Erik,Pannecouque, Christophe,Balzarini, Jan
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- Synthesis and on-target antibacterial activity of novel 3-elongated arylalkoxybenzamide derivatives as inhibitors of the bacterial cell division protein FtsZ
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Novel 3-elongated arylalkoxybenzamide derivatives were designed, synthesized and evaluated for their cell division inhibitory activity and antibacterial activity. Among them, the subseries of 3-alkyloxybenzamide derivatives exhibited greatly improved on-t
- Ma, Shutao,Ma, Siti,Cong, Chao,Meng, Xiaohui,Cao, Shasha,Yang, Hongkun,Guo, Yuanyuan,Lu, Xueyi
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supporting information
p. 4076 - 4079
(2013/07/25)
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- The synthesis and antibacterial activity of novel 3-o-arylalkylbenzamide derivatives as FtsZ inhibitors
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A series of novel 3-O-arylalkylbenzamide derivatives as FtsZ inhibitors was designed, synthesized and evaluated for their cell division inhibitory activity against B. subtilis and S. aureus, and in vitro antibacterial activity against various phenotypes o
- Ma, Shutao,Ma, Siti,Wang, Rongmei,Wang, Yuanze,Cao, Jichao
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p. 320 - 326
(2013/07/26)
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- Exploration of the chemical space of novel naphthalene-sulfonamide and anthranilic acid-based inhibitors of penicillin-binding proteins
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Penicillin-binding proteins are a well established, validated and still a very promising target for the design and development of new antibacterial agents. Based on our previous discovery of several noncovalent small-molecule inhibitor hits for resistant
- Sosic, Izidor,Turk, Samo,Sinreih, Masa,Trost, Nusa,Verlaine, Olivier,Amoroso, Ana,Zervosen, Astrid,Luxen, Andre,Joris, Bernard,Gobec, Stanislav
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scheme or table
p. 380 - 388
(2012/09/05)
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- Regiocontrolled rearrangement of isobenzofurans
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Regioselective alkylation and oxidative rearrangement of isobenzofurans has been achieved to generate substituted 4,8- ihydroxyisochromanones in good yields and with complete regiocontrol.
- Egan, Ben A.,Paradowski, Michael,Thomas, Lynne H.,Marquez, Rodolfo
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supporting information; experimental part
p. 2086 - 2089
(2011/06/25)
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- 4-[1-(Substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzenesulfonic acids: Synthesis, antimicrobial activity, QSAR studies, and antiviral evaluation
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A series of 4-[1-(substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]- benzene sulphonic acids (1-20) was synthesized and evaluated, in vitro, for their antimicrobial activity and the results indicated that compounds 4-[1-(4-Nitrobenzoyl)-1H-benzoimidazol-2-yl]-benzenesulfonic acid (9) and 4-(1-octadec-9-enoyl-1H-benzoimidazol-2-yl)-benzenesulfonic acid (18) were found to be the most active ones. QSAR investigations indicated that the multi-target QSAR model was effective in describing the antimicrobial activity over the one-target QSAR models. Further the mt-QSAR model indicated the importance of the topological parameter, Balaban index (J) followed by the electronic parameter, LUMO and topological parameter, valence second order molecular connectivity index (2χv) in describing the antimicrobial activity of synthesized compounds (1-20).
- Yadav, Snehlata,Kumar, Pradeep,De Clercq, Erik,Balzarini, Jan,Pannecouque, Christophe,Dewan, Sharwan Kumar,Narasimhan, Balasubramanian
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scheme or table
p. 5985 - 5997
(2011/01/13)
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- Antibacterial alkoxybenzamide inhibitors of the essential bacterial cell division protein FtsZ
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3-Methoxybenzamide is a weak inhibitor of the essential bacterial cell division protein FtsZ. Exploration of the structure-activity relationships of 3-methoxybenzamide analogues led to the identification of potent anti-staphylococcal compounds.
- Czaplewski, Lloyd G.,Collins, Ian,Boyd, E. Andrew,Brown, David,East, Stephen P.,Gardiner, Mihaly,Fletcher, Rowena,Haydon, David J.,Henstock, Vincent,Ingram, Peter,Jones, Clare,Noula, Caterina,Kennison, Leanne,Rockley, Chris,Rose, Valerie,Thomaides-Brears, Helena B.,Ure, Rebecca,Whittaker, Mark,Stokes, Neil R.
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scheme or table
p. 524 - 527
(2011/02/28)
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- ANTIBACTERIAL AGENTS
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Compounds of formula (I) have antibacterial activity wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is =C(R1)- or =N-; R1 is hydrogen or an optional substituent and R2 is hydrogen, methyl, or fluorine; or R1 and R2 taken together are -CH2-, -CH2CH2-, -O-, or, in either orientation, -O- CH2- Or -OCH2CH2-; R3 is a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, -N(CH2CH3)-, -C(=O)-, -O-(C=O)-, -C(=O)-O-, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk1 and Alk2 are optionally substituted C1C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radicals, which may optionally terminate with or be interrupted by -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, or -N(CH2CH3)-; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.
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Page/Page column 21
(2010/11/28)
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- 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES, PREPARATIONS THEREOF AND USES THEREOF
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Compounds of general formula (I) wherein D, E, R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification, as well as salts, enantiomers thereof and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
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Page/Page column 44-45
(2008/06/13)
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