cas 501-53-1, Benzyl chloroformate | Articles data

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Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer
Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.
Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao
p. 12089 - 12108
(2021/09/06)

Synthesis of N-trifluoromethyl amides from carboxylic acids
Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
supporting information
p. 2245 - 2255
(2021/08/12)

COMPOUNDS AND USES THEREOF
The present disclosure features compounds and methods useful for the treatment of BAF complex-related disorders.
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Page/Page column 157; 158

(2021/08/06)

Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions
Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.
Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon
supporting information
p. 12324 - 12332
(2020/08/06)

Photo-on-Demand Synthesis of Chloroformates with a Chloroform Solution Containing an Alcohol and Its One-Pot Conversion to Carbonates and Carbamates
Chloroformates are key reagents for synthesizing carbonates and carbamates. The present study reports a novel photo-on-demand in situ synthesis of chloroformates with a CHCl3 solution containing a primary alkyl alcohol. It further allowed the one-pot synthesis of carbonates and carbamates through subsequent addition of alcohols or amines, respectively.
Liang, Fengying,Suzuki, Yuto,Tsuda, Akihiko,Yanai, Masaki
supporting information

(2020/04/21)

Discovery of (3-Benzyl-5-hydroxyphenyl)carbamates as new antitubercular agents with potent in vitro and in vivo efficacy
A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625-6.25 μg/mL). The privileged compounds 3i and 3l showed moderate cytotoxicity against cell line A549. Compound 3l also exhibited potent in vivo inhibitory activity on a mouse infection model via the oral administration. The results demonstrated 3-hydroxyphenylcarbamates as a class of new antitubercular agents with good potential.
Cheng, Ya-Juan,Liu, Zhi-Yong,Liang, Hua-Ju,Fang, Cui-Ting,Zhang, Niu-Niu,Zhang, Tian-Yu,Yan, Ming
(2019/06/07)

Benzoxazin-4-ones as novel, easily accessible inhibitors for rhomboid proteases
Rhomboid proteases form one of the most widespread intramembrane protease families. They have been implicated in variety of human diseases. The currently reported rhomboid inhibitors display some selectivity, but their construction involves multistep synthesis protocols. Here, we report benzoxazin-4-ones as novel inhibitors of rhomboid proteases with a covalent, but slow reversible inhibition mechanism. Benzoxazin-4-ones can be synthesized from anthranilic acid derivatives in a one-step synthesis, making them easily accessible. We demonstrate that an alkoxy substituent at the 2-position is crucial for potency and results in low micromolar inhibitors of rhomboid proteases. Hence, we expect that these compounds will allow rapid synthesis and optimization of inhibitors of rhomboids from different organisms.
Yang, Jian,Barniol-Xicota, Marta,Nguyen, Minh T.N.,Ticha, Anezka,Strisovsky, Kvido,Verhelst, Steven H.L.
supporting information
p. 1423 - 1427
(2018/03/06)

Preparation method of alicyclic and aromatic-aliphatic chloroformate
The invention belongs to the technical field of fine chemistry, and in particular relates to a preparation method of alicyclic and aromatic-aliphatic chloroformate. The preparation method is characterized in that alicyclic alcohol chloroformate or aromatic-aliphatic alcohol chloroformate is obtained by taking alicyclic alcohol or aromatic-aliphatic alcohol and bis(trichlormethyl)carbonate as raw materials, taking organic base as a catalyst and reacting in an organic solvent under certain reaction temperature and certain reaction time, wherein molar ratio among the alicyclic alcohol or the aromatic-aliphatic alcohol, the bis(trichlormethyl)carbonate and the organic base is 1 to (0.4 to 1) to (1.2 to 3); experiment time and experiment temperature are different in two stages, in the first stage, the reaction temperature is -10 to 0 DEG C, and the reaction time is 2 to 5 hours; in the second stage, the reaction temperature is 0 to 25 DEG C, and the reaction time is 7 to 13 hours; a mass ratio between the organic solvent and the alicyclic alcohol or the aromatic-aliphatic alcohol is (10 to 25) to 1; residue in a reaction system is effectively treated, and reaction waste is also recycled and utilized. The preparation method disclosed by the invention has the characteristics of stable reaction, high reaction yield and product purity, environment protection of a reaction process, low production cost, less emission of three wastes, simpleness in preparation technology and easiness in industrialization.
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Paragraph 0062-0063; 0068-0069

(2017/05/16)

In vitro radical scavenging and cytotoxic activities of novel hybrid selenocarbamates
Novel selenocyanate and diselenide derivatives containing a carbamate moiety were synthesised and evaluated in vitro to determine their cytotoxic and radical scavenging properties. Cytotoxic activity was tested against a panel of human cell lines including CCRF-CEM (lymphoblastic leukaemia), HT-29 (colon carcinoma), HTB-54 (lung carcinoma), PC-3 (prostate carcinoma), MCF-7 (breast adenocarcinoma), 184B5 (non-malignant, mammary gland derived) and BEAS-2B (non-malignant, derived from bronchial epithelium). Most of the compounds displayed high antiproliferative activity with GI50 values below 10 μM in MCF-7, CCRF-CEM and PC-3 cells. Radical scavenging properties of the new selenocompounds were confirmed testing their ability to scavenge DPPH and ABTS radicals. Based on the activity of selenium-based glutathione peroxidases (GPxs), compounds 1a, 2e and 2h were further screened for their capacity to reduce hydrogen peroxide under thiol presence. Results suggest that compound 1a mimics GPxs activity. Cytotoxic parameters, radical scavenging activity and ADME profile point to 1a as promising drug candidate.
Romano, Beatriz,Plano, Daniel,Encío, Ignacio,Palop, Juan Antonio,Sanmartín, Carmen
p. 1716 - 1727
(2015/03/30)

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles
The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).
Diosdado, Saioa,Lopez, Rosa,Palomo, Claudio
supporting information
p. 6526 - 6531
(2014/06/09)

Further characterization of a putative serine protease contributing to the γ-secretase cleavage of β-amyloid precursor protein
The 3-alkoxy-7-amino-4-chloro-isocoumarins JLK-6 and JLK-2 have been shown to markedly reduce the production of Amyloid β-peptide (Aβ) by Amyloid-β Precursor Protein (APP) expressing HEK293 cells by affecting the γ-secretase cleavage of APP, with no effect on the cleavage of the Notch receptor. This suggested that these compounds do not directly inhibit the presenilin-dependent γ-secretase complex but more likely interfere with an upstream target involved in γ-secretase-associated pathway. The mechanism of action of these compounds is unknown and there are high fundamental and therapeutical interests to unravel their target. Isocoumarin compounds were previously shown to behave as potent mechanism-based irreversible inhibitors of serine proteases, suggesting that the JLK-directed target could belong to such enzyme family. To get further insight into structure-activity relationships and to develop more potent isocoumarin derivatives, we have synthesized and evaluated a series of isocoumarin analogues with modifications at positions 3, 4 and 7. In particular, the 7-amino group was substituted with either acyl, urethane, alkyl or aryl groups, which could represent additional interaction sites. Altogether, the results highlighted the essential integrity of the 3-alkoxy-7-amino-4-chloro-isocoumarin scaffold for Aβ-lowering activity and supported the involvement of a serine protease, or may be more generally, a serine hydrolase. The newly reported 7-N-alkyl series produced the most active compounds with an IC50 between 10 and 30 μM. Finally, we also explored peptide boronates, a series of reversible serine protease inhibitors, previously shown to also lower cellular Aβ production. The presented data suggested they could act on the same target or interfere with the same pathway as isocoumarins derivatives.
Peuchmaur, Marine,Lacour, Marie-Agnes,Sevalle, Jean,Lisowski, Vincent,Touati-Jallabe, Youness,Rodier, Fabien,Martinez, Jean,Checler, Frederic,Hernandez, Jean-Francois
p. 1018 - 1029
(2013/03/14)

SUBSTITUTED PYRIMIDINE AMMONIA COMPOUNDS AND USES THEREOF
The invention relates to substituted pyrimidine ammonia compounds. The structure of the compounds is represented as the general formula (I): The groups are as defined as specification. The compound represented by formula (I) can be used in the prevention of plants diseases caused by a plurality of pathogenic bacteria such as oomycota, basidiomycota, ascomycota, and fungi imperfecti, and due to these compounds have good bioactivity, which make them have very good effects at very low doses, especially more effective to powdery mildew of wheat. Therefore, the present invention relates to the use of the compounds having general formula I as fungicides, both in agriculture and other fields.
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Paragraph 0113; 0114

(2013/09/12)

1-(Hydroxyacetyl)pyrene a new fluorescent phototrigger for cell imaging and caging of alcohols, phenol and adenosine
1-(Hydroxyacetyl)pyrene has been introduced as a new fluorescent phototrigger for alcohols and phenols. Alcohols and phenols were protected as their corresponding carbonate esters by coupling with fluorescent phototrigger, 1-(hydroxyacetyl)pyrene. Photophysical studies of caged carbonates showed that they all exhibited strong fluorescence properties. Irradiation of the caged carbonates by visible light (≥410 nm) in aqueous acetonitrile released the corresponding alcohols or phenols in high chemical (95-97%) and quantum (0.17-0.21) yields. The mechanism for the photorelease was proposed based on Stern-Volmer quenching experiments and solvent effect studies. Importantly, 1-(hydroxyacetyl)pyrene showed as a phototrigger for rapid photorelease of the biologically active molecule adenosine. In vitro biological studies revealed that 1-(hydroxyacetyl)pyrene has good biocompatibility, cellular uptake property and cell imaging ability. The Royal Society of Chemistry and Owner Societies 2012.
Jana, Avijit,Saha, Biswajit,Ikbal, Mohammed,Ghosh, Sudip Kumar,Singh, N. D. Pradeep
p. 1558 - 1566
(2013/02/26)

Alkali-metal ion catalysis in alkaline ethanolysis of 2-pyridyl benzoate and benzyl 2-pyridyl carbonate: Effect of modification of nonleaving group from benzoyl to benzyloxycarbonyl
A kinetic study is reported on nucleophilic displacement reactions of benzyl 2-pyridyl carbonate 6 with alkalimetal ethoxides, EtOM (M = Li, Na, and K), in anhydrous ethanol at 25.0 ± 0.1 oC. The plots of pseudo-firstorder rate constant kobsd vs. [EtOM] curve upward, a typical phenomenon reported previously for alkaline ethanolysis of esters in which alkali-metal ions behave as a Lewis-acid catalyst. The kobsd value for the reaction of 6 with a fixed EtOK concentration decreases rapidly upon addition of 18-crown-6-ether (18C6), a complexing agent for K+ ion up to [18C6]/[EtOK] = 1.0 and then remains constant thereafter, indicating that the catalytic effect exerted by K+ ion disappears in the presence of excess 18C6. The reactivity of EtOM towards 6 increases in the order EtO- EtOLi EtONa EtOK, which is contrasting to the reactivity order reported for the corresponding reactions of 2-pyridyl benzoate 4, i.e., EtO- EtOK EtONa EtOLi. Besides, 6 is 1.7 and 3.5 times more reactive than 4 towards dissociated EtO- and ion-paired EtOK, respectively. The reactivity difference and the contrasting metal-ion selectivity are discussed in terms of electronic effects and transition-state structures.
Um, Ik-Hwan,Kang, Ji-Sun,Kim, Chae Won,Lee, Jae-In
body text
p. 519 - 523
(2012/05/04)

SAR development of lysine-based irreversible inhibitors of transglutaminase 2 for huntington's disease
We report a series of irreversible transglutaminase 2 inhibitors starting from a known lysine dipeptide bearing an acrylamide warhead. We established new SARs resulting in compounds demonstrating improved potency and better physical and calculated properties. Transglutaminase selectivity profiling and in vitro ADME properties of selected compounds are also reported.
Wityak, John,Prime, Michael E.,Brookfield, Frederick A.,Courtney, Stephen M.,Erfan, Sayeh,Johnsen, Siw,Johnson, Peter D.,Li, Marie,Marston, Richard W.,Reed, Laura,Vaidya, Darshan,Schaertl, Sabine,Pedret-Dunn, Anna,Beconi, Maria,MacDonald, Douglas,Mu?oz-Sanjuan, Ignacio,Dominguez, Celia
supporting information
p. 1024 - 1028
(2013/02/22)

AMINOPYRAZOLE DERIVATIVES
The invention relates to aminopyrazole derivatives of formula (I), wherein A, E, R1 and R2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.
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Page/Page column 27; 64

(2011/02/26)

Studies on the structure-activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 1: Tuning the N-substituents
A novel series of CCR5 antagonists has been identified, utilizing the lead, nifeviroc, which were further modified based on bioisosteric principles. Lead optimization was pursued by balancing potential toxicity and potency. Potent analogues with low toxic properties were successfully developed by formation of urea and amide bonds at the nitrogen at position 4- of the pyrrolidine ring.
Ben, Li,Jones, Eric Dale,Zhou, Enkun,Li, Chen,Baylis, Dean Cameron,Yu, Shanghai,Wang, Miao,He, Xing,Coates, Jonathan Alan Victor,Rhodes, David Ian,Pei, Gang,Deadman, John Joseph,Xie, Xin,Ma, Dawei
scheme or table
p. 4012 - 4014
(2010/08/19)

NOVEL VINBLASTINE DERIVATIVES, THEIR PREPARATION, USE AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAID DERIVATIVES
The invention provides vinblastine derivatives represented by the following formula 1 or their physiologically acceptable salts, their preparation, use and pharmaceutical compositions comprising the said derivatives. The said vinblastine derivatives show inhibiting activities against tumor cell lines and can be used as medicaments for treating malignant tumors.
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Page/Page column 46

(2009/12/05)

One-pot radiosynthesis of [13N]urea and [13N] carbamate using no-carrier-added [13N]NH3
The aim of this study was to develop a practical labeling method of [ 13N]ligands using no-carrier-added [13N]NH3 with high specific activity. [13N]urea analogues [13N]1a and [13N]2a or [13N]carbamate [13N]3a were synthesized by reacting isocyanate 5a, carbamoyl chloride 6a or chloroformate 7a with [13N]NH3. The precursors 5a-7a were prepared by treating amines 8a and 9a and alcohol 10a with triphosgene in situ. These reaction mixtures were not purified and were used directly for [ 13N]ammonolysis, respectively. Using the one-pot method, we synthesized [13N]carbamazepine ([13N]4), a putative positron emission tomography ligand for brain imaging. Copyright
Kumata, Katsushi,Takei, Makoto,Ogawa, Masanao,Kato, Koichi,Suzuki, Kazutoshi,Zhang, Ming-Rong
experimental part
p. 166 - 172
(2010/07/02)

Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions
DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).
Mizuno, Takumi,Iwai, Toshiyuki,Ishino, Yoshio
p. 9157 - 9163
(2007/10/03)

Process for preparing alkyl/aryl chloroformates
The present invention discloses an improved method for the preparation of alky/aryl chloroformates directly from alcohols and triphosgene. This method is simple, mild and efficient avoids use of hazardous phosgene. It can be used for the preparation of various aryl as well as alkyl chloroformates in excellent yields.
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Page/Page column 2

(2010/02/11)

Exploration of the P2-P3 SAR of aldehyde cathepsin K inhibitors
The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S2 and S3 subsites with a series of carbamate derivatized norleucine aldehydes substituted at the P2 and P3 positions afforded analogs with cathepsin K IC50s between 600nM and 130pM.
Boros, Eric E.,Deaton, David N.,Hassell, Anne M.,McFadyen, Robert B.,Miller, Aaron B.,Miller, Larry R.,Paulick, Margot G.,Shewchuk, Lisa M.,Thompson, James B.,Willard Jr., Derril H.,Wright, Lois L.
p. 3425 - 3429
(2007/10/03)

A Convenient Synthesis of Novel N′-tert-Butyl-N′-Substituted Benzoyl-N-(Substituted Phenyl)aminocarbonylhydrazines and Their Derivatives
N-tert-butyl-N-substituted benzoylhydrazines were prepared in two convenient procedures with good yields, subsequent reaction with substituted phenylisocyanates in 1,2-dichloroethane provided a series of novel N′-tert-butyl-N‰-substituted benzoyl-N-(substituted phenyl)aminocarbonylhydrazines. Further treatment with oxalyl chloride gave their derivatives in good yields. The title compounds exhibit moderate larvicidal activities and anticancer activities.
Wang, Qingmin,Huang, Runqiu
p. 255 - 264
(2007/10/03)

Non-phosgene synthesis of benzyl chloroformate (CbzCl)
A novel synthetic method for benzyl chloroformate (CbzCl) using carbon monoxide or carbonyl sulfide as a carbonyl source was established. Benzyl chloroformate was successfully synthesized by the chlorination using sulfuryl chloride of S-methyl O-benzyl carbonothioate, which was prepared by the carbonylation of benzyl alcohol with carbon monoxide and sulfur (or carbonyl sulfide) in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) followed by esterification using methyl iodide.
Mizuno, Takumi,Takahashi, Junko,Ogawa, Akiya
p. 7765 - 7767
(2007/10/03)

Benzyl chloroformate (CbzCl) synthesis using carbon monoxide as a carbonyl source
A novel non-phosgene synthetic method for benzyl chloroformate (CbzCl) was established. S-Methyl O-benzyl carbonothioates were prepared by the carbonylation of benzyl alcohols with carbon monoxide and sulfur (or carbonyl sulfide) in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) followed by esterification using methyl iodide in good yields. Then, CbzCl derivatives were successfully synthesized by the chlorination of S-methyl O-benzyl carbonothioates using sulfuryl chloride in excellent yields.
Mizuno, Takumi,Takahashi, Junko,Ogawa, Akiya
p. 10011 - 10015
(2007/10/03)

Synthesis and biological activity of novel N′-tert-butyl-N′-substituted benzoyl-N-(substituted phenyl)aminocarbonylhydrazines and their derivatives
Benzyl chloroformate was synthesised by the reaction of benzyl alcohol and triphosgene in good yield for the first time. N-tert-Butyl-N-substituted benzoylhydrazines were prepared in a new and convenient procedure with good yields. A series of novel N′-tert-butyl-N′-substituted benzoyl-N-(substituted phenyl)aminocarbonylhydrazines and their derivatives were synthesised and evaluated for molting hormone mimicking activity. The results of bioassays showed that the title compounds exhibit good larvicidal activities and toxicity assays indicated that the title compounds can induce a premature, abnormal and lethal larval molt. We have found that the title compounds possess potential anticancer activities.
Wang, Qingmin,Huang, Runqiu
p. 8881 - 8883
(2007/10/03)

A facile synthesis of azidoformate via chloroformate
This work synthesized chloroformates by slowly adding alcohols into a suspension of trichloromethyl chloroformate, instead of phosgene, along with activated charcoal in tetrahydrofuran. This chloroformylation yielded chloroformates in near quantitative yield. The subsequent reaction between chloroformates and sodium azide in dry acetone produced azidoformates in a high yield.
Wu, Pei-Lin,Su, Chia-Hao,Gu, Yi-Jeng
p. 271 - 274
(2007/10/03)

Plant growth inhibition using the R-isomer of esprocarb
Compositions for controlling growth of plant species, and methods for using the compositions, are disclosed. The compositions contain a single-isomer enantiomeric S-benzyl thiocarbamate and are particularly useful in controlling annual weeds associated with rice, soybeans and corn.
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(2008/06/13)

Derivatives of imidazole, their preparation process, the new intermediates obtained, their use as medicaments and the pharmaceutical compositions containing them
The invention relates to the products of formula (I): STR1 in which: R1 =represents hydrogen, aryl, arylcarbonyl, arylthio, alkylcarbonyl, R2, R3 represent in particular halogen, mercapto, acyl, carboxy, nitro, cyano, amino, carbamoyl, R4, --OR4 with R4 representing in particular hydrogen, alkyl, alkenyl, alkynyl, acyl, amino, --(CH2)m1 --S(O)m2 --X--R10 with m1=0 to 4, m2=0 to 2, X represents a single bond or --NH--, --NH--CO--, --NH--CO--NH--, and R10 represents alkyl, alkenyl or aryl, and Y represents optionally substituted aryl, these products being in all isomer forms and salts, their use as medicaments.
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(2008/06/13)

Synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles as biologically active heterocycles
2-(Benzimidazol-2'-yl) benzoyl hydrazide 1 when condensed with aromatic acids in the presence of POCl3 afforded 2-aryl-5-[2'-benzimidazol-2''-yl) phenyl]-1, 3, 4-oxadiazoles 2a-o. The acid hydrazide 1 on cyclisation with CNBr yield 2-amino-5-[2'-(benzimidazol-2''-yl-phenyl)-1, 3, 4-oxadiazole 3 which on reaction with aryl sulphonyl chlorides and substituted benzoyl chloride give the corresponding sulphonamides 4a-o and amides 5a-o, respectively. All the products have been evaluated in vitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37Rv.
Kagthara, Preeti R.,Shah, Niraj S.,Doshi, Rajeev K.,Parekh
p. 572 - 576
(2007/10/03)

Compositions for reducing abnormal stimulation of endothelin receptors and novel compounds
The invention relates to the new use and the new products of formula (I): STR1 in which: R1 =represents hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, formyl, cycloalkyl, optionally interrupted by heteroatoms, R2, R3 represent in particular halogen, mercapto, acyl, carboxy, nitro, cyano, amino, carbamoyl, R4, --OR4 with R4 representing in particular hydrogen, alkyl, alkenyl, alkynyl, acyl, amino, --(CH2)m1 --S(O)m2 --X--R10 with m1=0 to 4, m2=0 to 2, X represents a single bond or --NH--, --NH--CO--, --NH--CO--NH--, and R10 represents alkyl, alkenyl or aryl, and Y represents optionally substituted aryl, these products being in all the isomer forms and the salts, as medicaments.
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(2008/06/13)

(Aryltelluro)formates as precursors of alkyl radicals: Thermolysis and photolysis of primary and secondary alkyl (aryltelluro)formates
Alkyl (aryltelluro)formates are effective precursors of oxyacyl, methyl, and primary and secondary alkyl radicals. At room temperature, irradiation of a benzene solution of methyl (aryltelluro)-formates 10-12, 2-methylpropyl (aryltelluro)formates 14 and 15, octyl (phenyltelluro)formate (17), cyclohexyl (aryltelluro)formates 19 and 20, 3β-cholestanyl (aryltelluro)formates 22 and 23, cholesteryl (phenyltelluro)formate (24) and benzyl (phenyltelluro)formate (27) with a 250-W low-pressure mercury lamp leads to the formation of oxyacyl radicals (34), which can be trapped by diphenyl diselenide to give the corresponding alkyl (phenylseleno)formates 13, 16, 18, 21, 24, 26, and 28 with excellent overall conversions. Thermolysis of these telluroformates at 160 °C in the dark leads to the formation of methyl and primary and secondary alkyl aryl tellurides 36-43 in excellent yields. Presumably, these transformations involve oxyacyl radicals, which undergo subsequent decarboxylation at the elevated temperature to afford alkyl radicals, which become involved in further radical chemistry. When 1-(benzylseleno)-5-hexyl (phenyltelluro)formate (44) was thermolysed under these conditions, 2-methylselenane (45) was observed as the sole selenium-containing product, demonstrating the synthetic utility of (aryltelluro)formates as alkyl radical precursors.
Lucas, Mathew A.,Schiesser, Carl H.
p. 5754 - 5761
(2007/10/03)

Heat-sensitive recording materials and phenol compounds
Heat-sensitive recording materials contain an electron-donating chromogenic compound and an electron-attracting compound. The recording materials also contain at least one compound represented by the following formula: STR1 wherein R1 and R3 mean a hydrogen atom or an alkyl, aralkyl or aryl group, R2 and R4 denote an alkyl, alkenyl, aralkyl or aryl group, X1, X2, Y1 and Y2 stand for an oxygen or a sulfur atom, and --Z1 -- and --Z2 -- are a specific aromatic group. Also provided are phenol compounds represented by the following formula: STR2 wherein R1, R2, X1 and Y1 have the same meanings as defined above; R5 and R6 are a hydrogen or halogen atom or an alkyl, alkoxy, aralkyl, aryl or hydroxyl group; p and q stand for an integer of 1-4; R5 and R6 may be either the same or different when p and q represent an integer of 2 or greater; and --Z3 -- means a specific divalent group.
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(2008/06/13)

Complexes derived from platinum, their preparation and the pharmaceutical compositions which contain them
New complexes of general formula (I) in which R1 and R2 together form a saturated or unsaturated polycyclic carbocyclic radical containing 7 to 12 carbon atoms, or a saturated or partially saturated mono-, bi- or tricyclic heterocyclic radical containing 5 to 11 chain members and a hetero-atom chosen from oxygen, sulphur or nitrogen, which latter atom can optionally be substituted by an alkoxycarbonyl radical, and, X1 and X2 represent chlorine atoms or together form either a radical of structure: STR1 in which n is 0 to 2 and R6 and R7, which are identical or different, are hydrogen atoms or, when n=1, can be alkyl radicals or form, together with the carbon atom to which they are attached, a cyclobutyl radical, or a radical of structure: STR2 in which n, R6 and R7 are defined as above, or their salts where such exist, and their hydrates, their preparation and the pharmaceutical compositions which contain them. STR3
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(2008/06/13)

SYNTHESES DE CARBONATES ET CARBAMATES BENZYLIQUES ET ALLYLIQUES
Different methods for the preparation of carbonates and carbamates derived from 1-phenylethyl, 2-cyclohexenyl and 1-methyl-2-propenyl are described.These conmpounds have been synthesized by the reactions of alcohols, phenols or amines with chloroformiates, imidazolocarbonates or corresponding mixed p-nitrophenylcarbonates. It is shown that these reactions can also be used for the introduction of 1-phenylethyloxycarbonyl - (I), 2-cyclohexenyloxycarbonyl - (II) and 1-methyl-2-propenyloxycarbonyl - (III) groups into alcohols, phenols and amines for the protection of hydroxyls and amino-groups.
Kryczka, Boguslaw
p. 147 - 158
(2007/10/02)

Qunoline intermediates useful therein for synthesizing antibacterial compounds
A novel process and intermediates used therein for linking a cephalosporin compound to a quinolone are disclosed. According to the disclosed process, the 2-carboxylic acid moiety of the cephalosporin compound is treated with an organic base. The resulting salt is then reacted with a quinolone compound which has been activated using a haloformate. The reaction is run in a non-aqueous organic solvent. 4-Dimethylaminopyridine is used to promote the reaction between the cephalosporin salt and the activated quinolone.
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(2008/06/13)

CELL-DELIVERY AGENT
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(2008/06/13)

Process for hydrolyzing 2,6-dideoxy-2,6-iminoheptononitrile derivatives using trifluoroacetic acid and dinitrogen tetroxide
A procedure for the mild conversion of a carbonitrile to the corresponding carboxylic acid by first using trifluoroacetic acid in the presence of a catalytic amount of mercuric ion followed by oxidative hydrolysis with dinitrogen tetroxide is described herein. The use of this procedure in the preparation of 1,3,4,5-tetra-O-benzoyl-2,6-dideoxy-2,6-imino-D-glycero-L-gulo-heptitol hydrochloride is also described here.
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(2008/06/13)

Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds
There are described new condensed diazepinones of general formula STR1 wherein B represents one of the divalent groups STR2 and D represents the groups STR3 and X1, X2 represents a =CH-- group or, if B assumes the meaning of the divalent group S, U or W, they may also represent an N atom, A1 and A2 in general represent lower alkylene groups, Z represents a C--C bond or the groups, --O--, --S--, --CH2 --, or --(CH2)2 --; R represents hydrogen or methyl, R1 and R2 generally represent alkyl groups which, together with the nitrogen atom between them, may also form a saturated monocylic, heterocyclic group, R3 represents alkyl, chlorine or hydrogen, R4 represents hydrogen or methyl, R5 and R6 represent hydrogen, halogen or alkyl, R7 represents hydrogen, chlorine or methyl, R8 represents hydrogen or lower alkyl, R9 represents hydrogen, halogen, lower alkyl and R10 represents hydrogen or methyl and R12 represents branched or unbranched alkyl. The compounds of general formula I and the acid addition salts thereof may be resolved into their isomers. The compounds of formula I and their salts may be used as vagal pacemakers for the treatment of bradycardia and bradyarrhythmia.
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(2008/06/13)

Phenylalanine derivatives enhancing intestinal absorption of insulin in mice
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Amino,Kawada,Toi,Kumashiro,Fukushima
p. 4426 - 4434
(2007/10/02)

Cell-delivery agent
A photo-cleavable compound for delivery and release of a biologically active substance to selected target cells; the compound includes a binding partner for a specific cell-surface receptor of those target cells, the biologically active substance to be delivered, and a photo-cleavable bridge between the binding partner and the biologically active substance. When the compound is exposed to a heterogeneous population of target and non-target cells, it binds selectively to the receptors on the surface of the target cells. Exposing the compound to light of selected wave length cleaves it, yielding the active substance.
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(2008/06/13)

Derivatives of 2-(3-phenyl-2-aminopropionyloxy)-acetic acid
A compound having the general formula STR1 in which R represents a hydrogen atom or a hydroxyl radical, R1 represents a hydrogen atom or a methyl radical, and R2 represents a phenylethyl radical, a C1 -C16 alkyl radical, or a C6 -C16 monocyclic, polycyclic or alicyclic radical optionally bonded through a methylene radical, and its pharmaceutically acceptable acid addition salts, the formula (I) having the L-configuration when R is OH and when R and R1 are both hydrogen, and having the DL-configuration when R is hydrogen and R1 is methyl. These compounds and salts are useful as medicaments in human and veterinary medicine for cardiovascular and/or neurological treatment.
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(2008/06/13)

Carbamates
Carbamate compounds of the formula: in which CO.X.CO is the diacyl radical of a polybasic carboxylic acid, and R1 is an optionally substituted hydrocarbyl radical; more particularly, X is a member of the group consisting of a direct link, C1 to C4 alkylene groups, C2 to C3 alkenylene, o-phenylene and p-phenylene and R1 is a member of the group consisting of C1 to C18 alkyl, phenyl, chlorophenyl, nitrophenyl, cyclohexyl and benzyl. These carbamates are useful as cross-linking agents in natural rubbers or synthetic rubbers based on isoprene or butadiene polymers.
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(2008/06/13)

Benzimidazole derivatives, compositions thereof and method of use as anthelmintics
Benzimidazole derivatives are providing having the structure STR1 wherein R1 is lower alkyl, phenyl-lower alkyl, halo-lower alkyl, mono-lower alkylaminoalkyl, di-lower alkylaminoalkyl, and alkyl pyridinium halide, R2 and R3 may be the same or different and are hydrogen or lower alkyl, R4 is cycloalkyl or cycloalkenyl, and m is 0 to 3, n is 0 to 3, m + n being ≤5. These compounds are useful as anthelmintic agents.
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(2008/06/13)