cas 20776-50-5, 2-Amino-4-bromobenzoic acid

Articles about 20776-50-5Total 26 be found

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Legatte,Dunn
p. 1158,1166
(1965)
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Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality
A general and expedient method has been developed for the solid-phase synthesis of 1,4-benzodiazepine-2,5-diones 1 from three commercially available components; anthranilic acids, α-amino esters, and alkylating agents. Reaction conditions have been developed to prepare either racemic compounds for lead identification efforts or optically pure compounds for lead optimization efforts. The incorporation of diverse functionality into the benzodiazepine products has also been demonstrated. On the basis of the scope and generality of the synthesis sequence, a library of 1,4-benzodiazepine-2,5-diones has been prepared from 11 alkylating agents, 12 anthranilic acids, and 19 α-amino esters (nine sets of enantiomeric pairs and glycine methyl ester hydrochloride). The library was prepared in a spatially separate format using a microtiter-based apparatus that is inexpensive and straightforward to construct from ordinary items found in an organic or bioorganic laboratory. The high quality of the 1,4-benzodiazepine-2,5-dione library has been demonstrated by evaluating representative compounds by HPLC analysis and 1H NMR.
Boojamra,Burow,Thompson,Ellman
p. 1240 - 1256
(1997)
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Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease
Based on a multitarget strategy, a series of novel tacrine-pyrimidone hybrids were identified for the potential treatment of Alzheimer's disease (AD). Biological evaluation results demonstrated that these hybrids exhibited significant inhibitory activities toward acetylcholinesterase (AChE) and glycogen synthase kinase 3 (GSK-3). The optimal compound 27g possessed excellent dual AChE/GSK-3 inhibition both in terms of potency and equilibrium (AChE: IC50 = 51.1 nM; GSK-3β: IC50 = 89.3 nM) and displayed significant amelioration on cognitive deficits in scopolamine-induced amnesia mice and efficient reduction against phosphorylation of tau protein on Ser-199 and Ser-396 sites in glyceraldehyde (GA)-stimulated differentiated SH-SY5Y cells. Furthermore, compound 27g exhibited eligible pharmacokinetic properties, good kinase selectivity, and moderate neuroprotection against GA-induced reduction in cell viability and neurite damage in SH-SY5Y-derived neurons. The multifunctional profiles of compound 27g suggest that it deserves further investigation as a promising lead for the prospective treatment of AD.
Yao, Hong,Uras, Giuseppe,Zhang, Pengfei,Xu, Shengtao,Yin, Ying,Liu, Jie,Qin, Shuai,Li, Xinuo,Allen, Stephanie,Bai, Renren,Gong, Qi,Zhang, Haiyan,Zhu, Zheying,Xu, Jinyi
p. 7483 - 7506
(2021/06/28)

Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids
Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances,etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundanto-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines,etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.
Jiang, Xuefeng,Li, Yiming,Lin, Zhenyang,Wang, Yuhong,Yang, Tilong
supporting information
p. 2986 - 2991
(2021/05/05)

Anthranilic acid and derivatives thereof as well as synthesis method and application thereof
In the reaction solvent, o-methyl (hetero) aryl nitro compound is taken as a reaction raw material and is used for water. The anthranilic acid and its derivatives are synthesized by the action of a catalyst, a base and an additive. The synthetic method has the advantages of cheap and easily available raw materials, simple reaction operation, high yield and excellent functional group tolerance, and provides a simple and efficient method for synthesizing o-aminobenzoic acid which is widely used in the aspects of dyes, medicines, pesticides, spices and the like. The invention further discloses the anthranilic acid and derivatives and application thereof, and has a wide application prospect.
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Paragraph 0089-0091

(2021/09/15)

Controlled deposition of large-area and highly-ordered thin films: effect of dip-coating-induced morphological evolution on resistive memory performance
Developing a simple, versatile and efficient technique that enables both large-scale production and nano-scale control is highly desirable but very challenging for achieving high-performance organic-based memory electronic devices. Herein, we employed a dip-coating method to fabricate reliable and cost-effective organic memory devices (OMDs). This technique enables us to deposit high-quality, homogeneous and large-area nanopatterns on the surfaces of thin films and realize uniform OMD performances with a record reproducibility up to 96%. To the best of our knowledge, this is the first report on dip-coated OMDs with the highest reproducibility observed to date, which demonstrates the promising versatility of the dip-coating technique to fabricate organic memory devices and its suitability to scale-up for high-throughput solution processing.
Li, Yang,Zhang, Cheng,Li, Zhuang,Gu, Peiyang,Wang, Zilong,Li, Hua,Lu, Jianmei,Zhang, Qichun
supporting information
p. 3512 - 3521
(2019/03/27)

A kind of novel 4,5-substituted-7-carboxylic acid methyl ester indole dione derivatives and their use in anti-tumor drug
The invention relates to a kind of novel 4,5-substituted-7-methyl formate indoledione derivatives and an application thereof in anti-tumor drugs. The derivatives are 4-floro-5-bromo-7-methyl formate indoledione, 4-floro-5-nitro-7-methyl formate indoledione, 4-chloro-5-bromo-7-methyl formate indoledione, 4,5-dibromo-7-methyl formate indoledione and the like. In the invention, the kind of 4,5-substituted-7-methyl formate indoledione derivatives are synthesized and tested for the in-vitro tumor cell inhibition activity, and the result indicates that the kind of derivatives realize certain inhibition effects (IC5010muM) on the human leukemia cell (K562), human colon cancer cell (HT-29) and human liver cancer cell (HepG2) and have broad prospects in the development and application of anti-tumor drugs.
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(2017/02/24)

Discovery of 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine as a Potent IKur Inhibitor
A new series of phenylquinazoline inhibitors of Kv 1.5 is disclosed. The series was optimized for Kv 1.5 potency, selectivity versus hERG, pharmacokinetic exposure, and pharmacodynamic potency. 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine (13k) was identified as a potent and ion channel selective inhibitor with robust efficacy in the preclinical rat ventricular effective refractory period (VERP) model and the rabbit atrial effective refractory period (AERP) model.
Finlay, Heather J.,Johnson, James A.,Lloyd, John L.,Jiang, Ji,Neels, James,Gunaga, Prashantha,Banerjee, Abhisek,Dhondi, Naveen,Chimalakonda, Anjaneya,Mandlekar, Sandhya,Conder, Mary Lee,Sale, Harinath,Xing, Dezhi,Levesque, Paul,Wexler, Ruth R.
supporting information
p. 831 - 834
(2016/10/12)

A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C-H Amidation Using Azidoformates
Described herein is the development of Ir(III)-catalyzed direct C-H amidation using azidoformates as a readily deprotectable amino source. Substrates with unactivated methyl C(sp3)-H and aromatic or olefinic C(sp2)-H bonds were smoothly reacted by the iridium-based catalyst system to provide the corresponding primary alkylamines and anilines upon the subsequent removal of N-protecting groups, such as Boc, Fmoc, Cbz, pNZ, or Troc. A brief mechanistic study and synthetic applications are also presented.
Kim, Hyunwoo,Park, Gyeongtae,Park, Juhyeon,Chang, Sukbok
p. 5922 - 5929
(2016/09/09)

Substituted Amino-Pyrimidine Derivatives
The present application provides novel substituted quinazoline and pyrido-pyrimidine compounds and pharmaceutically acceptable salts, prodrugs, and solvates thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating PI3K and/or mTOR activity by administering a therapeutically effective amount of one or more of the compounds to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the PI3K/AKT/mTOR pathway. Advantageously, these compounds perform as dual PI3K/mTOR inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.
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(2014/02/16)

SUBSTITUTED QUINAZOLINE AND PYRIDO-PYRIMIDINE DERIVATIVES
The present application provides novel substituted quinazoline and pyrido- pyrimidine compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating PI3K and/or mTOR activity by administering a therapeutically effective amount of one or more of the compounds to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the PI3K/AKT/mTOR pathway. Advantageously, these compounds perform as dual PI3K/mTOR inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.
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(2012/05/19)

HETERO-BICYCLIC DERIVATIVES AS HCV INHIBITORS
Inhibitors of HCV replication of formula (I) including stereochemically isomeric forms, and salts, hydrates, solvates thereof, wherein R and R' have the meaning as defined herein. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other HCV inhibitors,in HCV therapy.
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Page/Page column 48

(2012/02/13)

A novel iodide-catalyzed reduction of nitroarenes and aryl ketones with H3PO2 or H3PO3: Its application to the synthesis of a potential anticancer agent
A novel iodide-catalyzed reduction method using hypophosphorous and/or phosphorus acids was developed to reduce both diaryl ketones and nitroarenes chemoselectively in the presence of chloro and bromo substituents in high yield. This efficient and practical method has been successfully applied to a large scale production of a potential anticancer agent
Wu, George G.,Chen, Frank X.,LaFrance, Danny,Liu, Zhijian,Greene, Scott G.,Wong, Yee-Shing,Xie, Ji
supporting information; experimental part
p. 5220 - 5223
(2011/12/04)

Design and mechanism of iron catalyzed carbon-carbon bond cleavage and N-oxidation processes of hazardous dyes for selective synthesis of nitroarenes and aminoarenecarboxylic acids
An efficient iron catalyzed oxidative degradation process has been developed for selective conversion of environmentally hazardous azo and indigo dyes into nitroarenes and aminoarenecarboxylic acids (anthranilic acids) respectively, using polymer supported tribromide reagent at an alkaline pH. The in situ generated and the isolated (defined) chloro-iron(II)-terpyridine- pyridine carboxylate [Fe(tpy)(pic)Cl] catalyst system has been developed and its catalytic function was invented for the degradation process. The different nitrogenous and oxygen ligands have been screened out for the development of best catalyst system, and eventually we explored pyridine 2-carboxylic acid and terpyridine ligands together, were found to be the best. Notably, the in situ generated and the defined catalyst systems have found to be more effective with similar catalytic activities towards the oxidative degradation of both the dyes. As a result, the whole oxidative degradation process has been carried out with Fe(tpy)(pic)Cl catalyst system and the general process utilizes the efficient catalytic method for the selective oxidation of -NN- and -CC- bonds of azo and indigo dyes respectively. The detailed catalysis, mechanistic and kinetic investigations have been made for the reactions. Interestingly, both the dyes proceed with a common oxidative degradation mechanism under identical kinetic patters. A common oxidative degradation mechanism which operates in both the dyes has been proposed and an identical related kinetic model was designed. The main interesting aspect of the present work pertains to the catalytic conversion of environmentally hazardous compounds into useful molecules; such are anthranilic acids and nitrobenzenes. Other special aspect related to catalytic activity of iron and potentially, iron catalyst accelerates the reaction rates with 15-20-fold faster. The reactions were also carried out with different polymer supported trihalide and inter-halide reagents. Notably, trichloride and inter-halide regents were found to be more reactive. The catalytic method developed for the degradation process was found to be very efficient and the involvement of cost-effective reagents makes the reaction simple, and can be conveniently scalable to industrial/technological operations with suitable modifications.
Jagadeesh, Rajenahally V.,Kiran,Bhagat, Pundlik R.,Kumar, S. Senthil,Nithya,Khan, F. Nawaz,Sivakumar
experimental part
p. 92 - 104
(2011/05/05)

A simple, safe and efficient synthesis of Tyrian purple (6,6'-Dibromoindigo)
6,6'-Dibromoindigo is a major component of the historic pigment Tyrian purple, arguably the most famous dye of antiquity. Over the last century, chemists have been interested in developing practical syntheses of the compound We describe herein a new, reasonably simple and efficient synthesis of Tyrian purple which opens the way to the production of large quantities of the dye with minimal hazards and at low cost.
Wolk, Joel L.,Frimer, Aryeh A.
experimental part
p. 5561 - 5580
(2010/12/20)

Bacterial translation inhibitors, 1-acylindazol-3-ols as anthranilic acid mimics
The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents has been described in a recent series of papers. This paper describes the discovery of 1-acylindazol-3-ols as a novel bioisostere of an anthranilic acid. The synthesis and structure-activity relationships of the indazol bioisosteres are described herein.
Stiff, Cory,Graber, David R.,Thorarensen, Atli,Wakefield, Brian D.,Marotti, Keith R.,Melchior, Earline P.,Sweeney, Michael T.,Han, Fusen,Rohrer, Douglas C.,Zurenko, Gary E.,Romero, Donna L.
scheme or table
p. 6293 - 6297
(2009/07/18)

PHARMACEUTICAL COMPOUNDS
The invention provides a compound of the formula (I) or a salt, solvate, tautomer or N-oxide thereof for use in the treatment or prophylaxis of a disease state or condition mediated by protein kinase A and/or protein kinase B, wherein the ring Q is a benzene ring; J2-J1 is N=CR7 or R1aN-CO; G is OH or NR5R6; E is CONR7, NR7CO, C(R8)=C(R8) or (X)m(CR8R8a)n where X is O, S or NR7; provided that when J2-J1 is R1aN-CO, E is other than NR7CO; m and n are each 0 or 1, where m + n = 1 or 2; A is a bond and R4 and R4a are absent, or A is a saturated optionally substituted C1-7 hydrocarbon linker group having a maximum chain length of 5 atoms extending between E and G, one carbon atom in the linker group A being optionally replaced by O or N; R1,Rla, R2, and R3 are each H; halogen; C1-6 hydrocarbyl optionally substituted by halogen, OH or C1-2 alkoxy; CN; CONHR8; NH2; NHCOR10 or NHCONHR10; R4 is H or C1-4 alkyl; R4a is H, C1-4 alkyl or a group R9; R5 and R6 are each selected from H, R9 and C1-4 hydrocarbyl optionally substituted by halogen, C1-2 alkoxy or R9;or NR5R6 forms a saturated 4-7 membered monocyclic heterocyclic group; R7 is H or C1-4 alkyl; R8 and R8a each H or saturated C1-4 hydrocarbyl optionally substituted by fluorine; R9is a monocyclic or bicyclic carbocyclic or heterocyclic group containing up to 3 ring heteroatoms selected from N, O and S; or R4, R4a and A together form a saturated monocyclic 4-7 membered heterocycle; or NR5R6, R4 and A form a saturated 4-7 membered monocyclic heterocycle; or R4,together with R7 or R8 and A and E form a 4-7 membered saturated monocyclic heterocycle; or NR5R6 and R7 or R8 together with A and E form a 4-7 membered saturated monocyclic heterocycle; and R10 is optionally substituted phenyl or benzyl.
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Page/Page column 111; 144

(2010/11/30)

SUBSTITUTED QUINAZOLONES AS ANTI-CANCER AGENTS
The invention relates to chemical compounds of the formula (I): or pharmaceutically acceptable salts thereof, which possess B Raf inhibitory activity and are accordingly useful for their anti cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use in the production of an anti-cancer effect in a warm blooded animal such as man.
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Page/Page column 66

(2010/02/15)

Inhibition of FGFR3 and treatment of multiple myeloma
Methods of inhibiting fibroblast growth factor receptor 3 and treating various conditions mediated by fibroblast growth factor receptor 3 are provided that include administering to a subject a compound of Structure I, a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer. Compounds having the Structure I have the following structure where and have the variables described herein. Such compounds may be used to prepare medicaments for use in inhibiting fibroblast growth factor receptor 3 and for use in treating conditions mediated by fibroblast growth factor receptor 3 such as multiple myeloma.
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(2008/06/13)

Combination therapy with CHK1 inhibitors
Compounds of Structure I, and salts, tautomers, stereoisomers, and mixtures thereof may be used in methods of inhibiting checkpoint kinase 1 in subjects, in methods for inducing cell cycle progression, and in methods for increasing apoptosis in cells. Such compounds may be used to prepare pharmaceutical compositions and may be used in conjunction with DNA damaging agents.
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(2008/06/13)

Quinazoline derivatives
A compound of the formula (I) or a pharmaceutically acceptable salt thereof, a hydrate thereof, a solvate thereof, an optically active compound thereof, a racemate thereof or a diastereomer mixture thereof has a superior tyrosine-specific protein kinase inhibitory activity and is useful as a pharmaceutical agent, particularly as an agent for the prophylaxis or treatment of various cancers, psoriasis or diseases caused by arteriosclerosis, and the like.
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Page/Page column 31

(2010/02/07)

Sulfonamides having antiangiogenic and anticancer activity
Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.
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Page 38

(2008/06/13)

BENZIMIDAZOLE QUINOLINONES AND USES THEREOF
Methods of inhibiting various enzymes and treating various conditions are provided that include administering to a subject a compound of Structure I or IB, a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer. Compounds having the Structure I and IB have the following structures and have the variables described herein. Such compounds may be used to prepare medicaments for use in inhibiting various enzymes and for use in treating conditions mediated by such enzymes.
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Page 321

(2008/06/13)

Sulfonamides having antiangiogenic and anticancer activity
Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.
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(2008/06/13)

FUSED-RING PYRIMIDIN-4(3H)-ONE DERIVATIVES, PROCESSES FOR THE PREPARATION AND USES THEREOF
AbstractNovel compounds of the following formula (I) and pharmacologically acceptable salt and esters thereof can modulate LXR function and as a result show excellent anti-arteriosclerotic and anti-inflammatory activity:wherein:A represents aryl or heteroaryl;R1, R2 and R3 are the same or different and each represents hydrogen, hydroxyl, nitro, cyano, amino, halogen, carboxy, carbamoyl, mercapto, alkyl, haloalkyl, alkylcarbonyloxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, N-(alkylcarbonyl)-N-(alkyl)amino, alkoxycarbonylamino, N-(alkoxycarbonyl)-N-(alkyl)amino, alkylsulfonylamino, N-(alkylsulfonyl)-N-(alkyl)amino, haloalkylsulfonylamino, N-(haloalkylsulfonyl)-N-(alkyl)amino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, or R1 and R2 together are alkylenedioxy;R4 and R5 are the same or different and each represents hydrogen, hydroxyl, amino, halogen, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl or alkylthio;X represents hydrogen, hydroxyl, halogen, alkoxy or haloalkoxy; andY represents an optionally substituted alkyl, cycloalkyl, heterocyclyl, aryl, cycloalkylalkyl, heterocyclylalkyl or aralkyl group.
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Page 364

(2010/02/06)

Process for the preparation of haloanthranilic acids
The present invention relates to a process for the preparation of compounds of the general formula I STR1 in which X and Y, independently of each other, represent hydrogen, fluorine, chlorine or bromine, but cannot simultaneously represent hydrogen, characterised in that compounds of the general formula II STR2 in which X and Y are defined as above, are reacted with aqueous ammonia under copper catalysis, and to intermediates for the preparation of compounds of the general formula I.
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(2008/06/13)

Bromoderivatives of gramines. Preparation and pharmacological properties
Bromination of gramine (I), 1-methylgramine (IX), 2-methylgramine (IV) and 1,2-dimethylgramine (XV) with different mole ratios of bromine to substrate was investigated; it was seen that the 5- and 6-position are the normal sites of bromination and 1-methylgramines (IX) and (XV) give better yields of bromoderivatives.Among the compounds submitted the pharmacological screening, 2,6-dibromo-1-methylgramine hydrobromide (Xa) and especially 6-bromo-2-methylgramine (V) showed a clear antiserotoninic antiinflammatory and analgesic activity.Furthermore gramine (V) showed a good anti prostaglandin synthetase activity in vitro.Key-words: Bromogramines. - Antiserotonic activity. - Antiinflammatory activity.
Franzone, Jose Sebastian,Cirillo, Rocco,Cravanzola, Carlo
p. 261 - 268
(2007/10/02)