cas 2493-02-9, 4-BROMOPHENYL ISOCYANATE | Articles data

Articles about 2493-02-9Total 28 be found

Article title
Article abstract
Author
Journal number and time
Download

Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus
Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78–22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.
Ruan, Banfeng,Zhang, Yuezhou,Tadesse, Solomon,Preston, Sarah,Taki, Aya C.,Jabbar, Abdul,Hofmann, Andreas,Jiao, Yaqing,Garcia-Bustos, Jose,Harjani, Jitendra,Le, Thuy Giang,Varghese, Swapna,Teguh, Silvia,Xie, Yiyue,Odiba, Jephthah,Hu, Min,Gasser, Robin B.,Baell, Jonathan
supporting information

(2020/02/04)

Sulfonylurea dehydroabietate compound and preparation method and application thereof
The invention discloses a sulfonylurea dehydroabietate compound and a preparation method and application thereof. The compound has a chemical structural formula represented by a formula shown in the description, wherein R1 is 2-Br, 3-Br, 4-Br, 4-OCH3, 4-F, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl or H, and 2, 3 and 4 represent 2, 3 and 4 substituent sites on a benzene ring. The preparation method of the compound comprises the following steps synthesizing sulfonyl chloride dehydroabietate; synthesizing sulfonamide dehydroabietate; synthesizing substituted phenyl isocyanate; synthesizing N'-substituted phenyl-12-sulfonylurea dehydroabietate. The compound disclosed by the invention has better activity and low toxicity and provides a better lead compound for developing antitumor drugs.
-
Paragraph 0062; 0064; 0068

(2019/02/04)

2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone compounds and application thereof
The invention belongs to the technical field of medicines and relates to 2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone compounds and an application thereof. 2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone derivatives comprise stereisomers and pharmaceutically applicable salts of the compounds and have the general structural formula shown in the description, wherein R is described inthe claims and description. The 2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone derivatives and pharmaceutically applicable acid-added salts of the compounds can be combined with existing medicines or used separately to serve as influenza virus inhibitors to treat influenza and have better curative effects on various type-A influenza in particular.
-
Paragraph 0049; 0063

(2018/04/21)

Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
supporting information
p. 13441 - 13445
(2018/09/21)

Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin
Nematodes are serious constraints of crop production worldwide. However, the traditional nematicides suffer from the side-effects, including environmental and human toxicity. Herein, more than 70 novel piperazinedione derivatives based on the natural product Barettin were synthesized and evaluated against the root-knot nematode Meloidogyne incognita (M. incognita). While most of synthesized compounds exhibited certain nematicidal activity at high concentration, the best one showed a nematicidal activity of 75% at 2.4 μmol/L.
Sun, Haiyang,Li, Hui,Wang, Jiayi,Song, Gonghua
p. 977 - 980
(2017/11/16)

Copper-catalyzed N[sbnd]H/S[sbnd]H functionalization: A strategy for the synthesis of benzothiadiazine derivatives
A copper-mediated N[sbnd]S bond-forming reaction via N[sbnd]H/S[sbnd]H activation is described. This reaction occurs under mild conditions with high efficiency, step economy, and tolerates a wide variety of functional groups, providing an efficient means of accessing biologically important 1,2,4-benzothiadiazin-3(4H)-ones.
Do?an, ?engül Dilem
p. 2217 - 2224
(2017/03/24)

DGAT1 INHIBITOR AND PREPARATION METHOD AND USE THEREOF
The present invention discloses a novel DGAT1 inhibitor, especially the compound of formula (I) or a pharmaceutically acceptable salt thereof, preparation and pharmaceutical composition thereof, as well as their uses in the preparation of a medicament for the prevention and treatment of Familial hyperchylomicronemia (FCS), obesity, hyperlipoproteinemia or hypertriglyceridemia.
-
Paragraph 0199; 0200

(2016/08/23)

A 10th factor inhibitor and its preparation method and application (by machine translation)
The invention relates to a 10th factor inhibitor and its preparation and application, the 10th factor inhibitor has the structure of formula I, the invention inhibitors to alpha-amino acid as a template, respectively through the amide, carbamate, or urea to the branched chain is formed by a series of novel structure of the compound, this kind of compound can be effectively with the 10th factor binding, prevent the formation of thrombus. (by machine translation)
-
Paragraph 0155; 0156

(2016/10/08)

Rhenium-catalyzed C-H aminocarbonylation of azobenzenes with isocyanates
The first C-H aminocarbonylation of azobenzenes with isocyanates is achieved by using rhenium-catalysis, which provides an expedient and atom-economical access to varied o-azobenzamides from readily available starting materials. The reaction efficiency can be enhanced by the catalytic use of sodium acetate via accelerated C-H bond activation.
Geng, Xiaoyu,Wang, Congyang
supporting information
p. 7619 - 7623
(2015/07/15)

Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions
A new synthetic approach for phenylurea derivatives involving the cross coupling of N-aryl formamides with amines through the formation of isocyanate intermediates in the presence of hypervalent iodine reagents is described.
Reddy, Nagireddy Veera,Kumar, Pailla Santhosh,Reddy, Peddi Sudhir,Kantam, Mannepalli Lakshmi,Reddy, Kallu Rajender
supporting information
p. 805 - 809
(2015/02/19)

One-pot and novel route for the synthesis of 4-substituted-1,2,4- triazolidine-3,5-diones
The efficient and one-pot synthesis of 4-substituted-1,2,4-triazolidin-3,5- dione derivatives (4-substituted urazoles) via combination of triphosgene, substituted anilines, and ethyl carbazate in the presence of cesium carbonate is presented.
Ghorbani-Choghamarani, Arash,Nikoorazm, Mohsen,Azadi, Gouhar
supporting information
p. 451 - 454
(2014/03/21)

Metal free oxidative coupling of aryl formamides with alcohols for the synthesis of carbamates
A direct transformation of N-aryl formamides to the corresponding carbamates via the formation of isocyanate intermediates is achieved in good yields using hypervalent iodine as an oxidant. This journal is
Reddy, N. Veera,Prasad, K. Rajendra,Reddy, P. Sudhir,Lakshmi Kantam,Reddy, K. Rajender
supporting information
p. 2172 - 2175
(2014/04/03)

N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
Yoganathan, Sabesan,Miller, Scott J.
supporting information
p. 602 - 605
(2013/04/11)

Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors
A number of 1,2-benzisothiazol-3-one derivatives were prepared through structural modification of the original compound from high-throughput screening. Some analogues (e.g., 6b, 6r, 6s and 6w) were identified as novel and potent caspase inhibitors with IC50 of nanomolar. Structure-activity relationship (SAR) studies for caspase-3 inhibition were evaluated in vitro. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The present small molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.
Liu, Dazhi,Tian, Zhen,Yan, Zhihui,Wu, Lixin,Ma, Yan,Wang, Quan,Liu, Wei,Zhou, Honggang,Yang, Cheng
p. 2960 - 2967
(2013/07/28)

Structure-activity relationship studies of pyrazolo[3,4-d]pyrimidine derivatives leading to the discovery of a novel multikinase inhibitor that potently inhibits FLT3 and VEGFR2 and evaluation of its activity against acute myeloid leukemia in vitro and in vivo
We describe the structural optimization of a hit compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl)-3-(3-methoxyphenyl)urea (1), which exhibits inhibitory activity but low potency against FLT3 and VEGFR2. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis using cell- and transgenic-zebrafish- based assays led to the discovery of a number of compounds that exhibited both high potency against FLT3-driven human acute myeloid leukemia (AML) MV4-11 cells and a considerable antiangiogenic effect in transgenic-zebrafish-based assays. The compound 1-(4-(1H-pyrazolo[3,4-d]pyrimidin -4-yloxy)phenyl)-3-(4-chloro-3- (trifluoromethyl)phenyl)urea (33), which exhibited the highest activity in preliminary in vivo anti-AML assays, was chosen for further anti-AML studies. The results demonstrated that compound 33 is a multikinase inhibitor that potently inhibits FLT3 and VEGFR2. In an MV4-11 xenograft mouse model, a once-daily dose of compound 33 at 10 mg/kg for 18 days led to complete tumor regression without obvious toxicity. Western blot and immunohistochemical analyses were performed to determine the mechanism of action of compound 33.
Yang, Ling-Ling,Li, Guo-Bo,Ma, Shuang,Zou, Chan,Zhou, Shu,Sun, Qi-Zheng,Cheng, Chuan,Chen, Xin,Wang, Li-Jiao,Feng, Shan,Li, Lin-Li,Yang, Sheng-Yong
supporting information
p. 1641 - 1655
(2013/04/10)

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine
Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.
Zhou, Shuguang,Yao, Ting,Yi, Jicheng,Li, Dashuai,Xiong, Jing
p. 315 - 319
(2013/07/27)

Specific inhibitors of puromycin-sensitive aminopeptidase with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton
Specific puromycin-sensitive aminopeptidase (PSA) inhibitors with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton were prepared and their structure-activity relationships were investigated. The nature (F, Cl or Br), number and position(s) of the halogen atom(s) introduced into the 3-phenyl group were concluded to be critical determinants of the inhibitory activity.
Matsumoto, Yotaro,Noguchi-Yachide, Tomomi,Nakamura, Masaharu,Mita, Yusuke,Numadate, Akiyoshi,Hashimoto, Yuichi
p. 1449 - 1463
(2013/08/23)

(Tosylimino)phenyl-λ3-iodane as a reagent for the synthesis of methyl carbamates via hofmann rearrangement of aromatic and aliphatic carboxamides
A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.
Yoshimura, Akira,Luedtke, Matthew W.,Zhdankin, Viktor V.
experimental part
p. 2087 - 2091
(2012/05/05)

Synthesis of aryl urea derivatives from aryl amines and aryl isocyanates
The present study describes the synthesis of novel diaryl urea derivatives derived from aryl amine and aryl isocyanates. The synthesized compounds are analogs of sorafenib [4-[4-[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl] amino]phenoxy]-N-methylpyridine-2- carboxamide] having potential antiproliferative activity.
Usharani,Bhujanga Rao,Reddy,Dubey
experimental part
p. 1802 - 1806
(2011/12/22)

1-propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the Lossen rearrangement: Application to the synthesis of urea and carbamate derivatives
The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the corresponding ureas and carbamates. Georg Thieme Verlag Stuttgart New York.
Vasantha, Basavalingappa,Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
experimental part
p. 2990 - 2996
(2010/10/21)

Synthesis, biological activity, and molecular modeling investigation of new pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as human A3 adenosine receptor antagonists
A new series of pyrazolotriazolopyrimidines bearing different substitutions on the phenylcarbamoyl moieties at the N5 position, being highly potent and selective human A3 adenosine receptor antagonists, is described. The compounds represent an extension and an improvement of our previous work on this class of compounds (J. Med. Chem. 1999, 42, 4473-4478; J. Med. Chem. 2000, 43, 4768-4780). All the synthesized compounds showed A3 adenosine receptor affinity in the subnanomolar range and high levels of selectivity in radioligand binding assays at the human A1, A2A, A2B, and A3 adenosine receptors. In particular, the effect of the substitution and its position on the phenyl ring have been studied. From binding data, it is evident that the unsubstituted derivatives on the phenyl ring (e.g., compound 59, hA3 = 0.16 nM, hA1/hA3 = 3713, hA2A/hA3 = 2381, hA2B/hA3 = 1388) showed the best profile in terms of affinity and selectivity at the human A3 adenosine receptors. The introduction of a sulfonic acid moiety at the para position on the phenyl ring was attempted in order to design water soluble derivatives. However, this substitution led to a dramatic decrease of affinity at all four adenosine receptor subtypes. A computer-generated model of the human A3 receptor was built and analyzed to better interpret these results, demonstrating that steric control, in particular at the para position on the phenyl ring, plays a fundamental role in the receptor interaction. Some of the synthesized compounds proved to be full antagonists in a specific functional model, where the inhibition of cAMP-generation by IB-MECA was measured in membranes of CHO cells stably transfected with the human A3 receptor with IC50 values in the nanomolar range, with a statistically significative linear relationship with the binding data.
Baraldi, Pier Giovanni,Cacciari, Barbara,Moro, Stefano,Spalluto, Giampiero,Pastorin, Giorgia,Da Ros, Tatiana,Klotz, Karl-Norbert,Varani, Katia,Gessi, Stefania,Borea, Pier Andrea
p. 770 - 780
(2007/10/03)

The first isolation of α-hydroperoxy-N-arylimidoyl cyanides from 2- arylamino-2-alkenenitriles (α-cyanoenamines)
Treatment of N-1-(2-chloroalkylidene)arylamines 6 with KCN in CH3CN at reflux afforded 2-arylamino-2-alkenenitriles 3 (42-58%), which underwent autoxidation, yielding the corresponding α-hydroperoxyimidoyl cyanides (95- 100%). (C) 2000 Elsevier Science Ltd.
Yun, Sangmin,Kim, Kyongtae
p. 1469 - 1473
(2007/10/03)

Novel carbamates as potent histamine H3 receptor antagonists with high in vitro and oral in vivo activity
The known histamine H3 receptor antagonists burimamide, thioperamide, clobenpropit, and a related homohistamine thioamide derivative were taken as templates in search for new leads. Novel histamine H3 receptor antagonists structurally described as carbamate derivatives of 3-(1H-imidazol-4- yl)propanol were prepared in high yields by treatment of the alcohol with corresponding isocyanates or carbamoyl chlorides and investigated for their H3 receptor antagonist activity. Different chain lengths and various substituents possessing different electronic and steric parameters were introduced and structure-activity relationships established. In different functional tests, the new antagonists showed high H3 receptor antagonist potencies in vitro (-log K(i) values of 6.4-8.4) at synaptosomes of rat cerebral cortex and low activities at histamine H1 and H2 receptor subtypes. They were also screened for their central in vivo activity in mice after peroral administration. The most promising compounds (2, 16, 19) showed ED50 values of about 1-2 mg/kg and thus are potential drugs for the therapy of H3 receptor dependent diseases. Some of the novel carbamate derivatives are H3 receptor selective compounds with high in vitro and in vivo activity.
Stark, Holger,Purand, Katja,Ligneau, Xavier,Rouleau, Agnès,Arrang, Jean-Michel,Garbarg, Monique,Schwartz, Jean-Charles,Schunack, Walter
p. 1157 - 1163
(2007/10/03)

Parasiticidal new substituted thienopyranones
Parasiticidal new substituted thienopyranones of the formula STR1 in which X represents O or S, R1 and R2 independently of one another represent hydrogen, halogen, CN, NO2, alkyl, aralkyl, aryl, alkylcarbonyl or alkoxycarbonyl, or, together with the adjacent C atoms, form a carbocyclic ring which is optionally interrupted by heteroatoms, R3 represents optionally substituted alkyl or phenyl, R4 represents hydrogen or alkyl, R3 and R4, together with the adjacent nitrogen atom, represent a heterocyclic 5- or 6-membered ring. Some of the intermediates for making them are also new.
-
(2008/06/13)

URETHANES IN THE SYNTHESIS OF ARYL ISOCYANATES
-
Rakhimov, D. N.,Abdullaev, N. P.,Shakhidoyatov, Kh. M.
p. 795 - 796
(2007/10/02)

Process for the synthesis of isocyanates and of isocyanate derivatives
The present invention relates to a process for the synthesis of isocyanates and of isocyanate derivatives. Isocyanates are obtained by reacting an organic halide with a metal cyanate in an organic medium in the presence of a catalyst consisting of a complex of nickel with at least one organic ligand, in which complex the nickel is in the zero oxidation state. A carbamate or a urea, respectively, are obtained by a subsequent reaction with a hydroxy compound or a primary or secondary amine. Isocyanates and their derivatives are used especially either as refined synthesis agents for the production of pesticides and medications, or as monomers or comonomers for the preparation of many macromolecular compounds.
-
(2008/06/13)

Mass Spectral Study of N-(1,2,3-Triazol-1-yl)-N'-arylureas
The fragmentation pattern upon electron impact at 70 eV of several N-(1,2,3-triazol-1-yl)ureas as well as of the corresponding N'-aryl substituted is studied.The spectra examined contain the molecular ion peak in very low intensity and in some cases is absent, whereas the ion ArNCO+. is the base peak or one of the most prominent.The principal fragmentation pathway takes place via the + ion.
Adamopoulos, S.,Alexandrou, N. E.
p. 145 - 148
(2007/10/02)