- Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions
-
Mutation of the proto-oncogene K-Ras is one of the most common molecular mechanisms in non-small cell lung cancer. Many drugs for treating lung cancer have been developed, however, due to clinical observed K-Ras mutations, corresponding chemotherapy and targeted therapy for such mutation are not efficient enough. In this study, on the basis of the crystal structure of K-Ras, 21 analogues (TKR01–TKR21) containing urea or thiourea were rationally designed, which can effectively inhibit the lung cancer cell A549 growth. The designing of these compounds was based on the structure of K-Ras protein, and the related groups were replaced by bioisosteres to improve the affinity and selectivity. Biological testing revealed that compound TKR15 could significantly inhibit the proliferation of A549 cell with IC50 of 0.21 μM. Docking analysis showed that the TKR15 can effectively bind to the hydrophobic cavity and form a hydrogen bond with the Glu37. In addition, through flow apoptosis assay and immunofluorescence staining assay, it confirmed that this compound can inhibit A549 cell proliferation with the mechanism of blocking K-RasG12V protein and effector proteins interactions through the apoptotic pathway. In conclusion, our studies in finding novel potent compound (TKR15) with confirmed mechanism showed great potential for further optimisation and other medicinal chemistry relevant studies.
- Cheng, Minghui,Meng, Xin,Tang, Haikang,Xu, Wenqing,Yang, Fujun,Zhang, Yuan
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p. 344 - 353
(2019/12/30)
-
- Synthesis and biological evaluation of innovative thiourea derivatives as PHGDH inhibitors
-
In order to discover novel compounds with inhibitory activity against 3-phosphoglycerate dehydrogenase (PHGDH), a series of thiourea derivatives were designed and synthesized based on the structural modification of compound 5d. Compound 5d emerged from the visual database of ChemDiv of 200,000 small molecules by docking score ranking. Inhibition experiments on PHGDH activity of newly synthesized compounds were performed in vitro. Compounds with more than 30percent inhibitory rate at 25?μM on PHGDH were screened for IC50 measurement. Anti-proliferative activity of 4a, 5a, 6e, 6n against A2780, MDA-MB-468, MDA-MB-231 and HEK293T in vitro was evaluated. The results showed that the compound 4a displayed the best inhibitory activity on PHGDH among the newly synthesized compounds, and the compounds 4a, 5a, 6n had a better proliferation inhibition effect on human A2780 cell line than NCT-503 reported previously. In addition, 2D interaction diagrams revealed potential action modes of active compounds with PHGDH.
- Xiang, Jiawei,Tao, Lei,Zhou, Yue,Tan, Yuping,Li, Zicheng,Zhao, Yinglan,Sun, Qingxiang,Luo, Youfu
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p. 3873 - 3886
(2020/05/29)
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- Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur
-
A copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur in the absence of organophosphine has been established. This approach represents a simple and efficient one-pot synthesis of isothiocyanates, and features excellent functional group tolerance and the use of a cheap, safe and odorless sulfur source. Moreover, this process could directly provide isothiocyanate analogous bioactive molecules, thiocarbonyl-containing pesticides and facile construction of benzoxazole and benzimidazole frames.
- Feng, Wei,Zhang, Xing-Guo
-
supporting information
p. 1144 - 1147
(2019/01/28)
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- Isothiocyanate synthesized by three components and preparation method of isothiocyanate
-
The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.
- -
-
Paragraph 0034
(2019/04/26)
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- Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
-
We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
- Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
-
supporting information
p. 4484 - 4491
(2018/10/17)
-
- Isothiocyanation of amines using the Langlois reagent
-
The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.
- Liao, Yan-Yan,Deng, Jian-Chao,Ke, Yan-Ping,Zhong, Xiao-Lin,Xu, Li,Tang, Ri-Yuan,Zheng, Wenxu
-
supporting information
p. 6073 - 6076
(2017/07/10)
-
- Synthesis, structure-activity relationship and binding mode analysis of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase
-
A series of 4-thiazolidinone derivatives were synthesized and evaluated as novel human dihydroorotate dehydrogenase (hDHODH) inhibitors. Compounds 26 and 31 displayed IC50 values of 1.75 and 1.12 μM, respectively. The structure-activity relationship was summarized. Further binding mode analysis revealed that compound 31 could form a hydrogen bond with Tyr38 and a water-mediated hydrogen bond with Ala55, which may be necessary for maintaining the bioactivities of the compounds in this series. Further structural optimization of the para- or meta-position of the phenyl group at R will lead to the identification of more potent hDHODH inhibitors.
- Zeng, Fanxun,Qi, Tiantian,Li, Chunyan,Li, Tingfang,Li, Honglin,Li, Shiliang,Zhu, Lili,Xu, Xiaoyong
-
supporting information
p. 1297 - 1302
(2017/07/07)
-
- Alkali-free green synthetic isothiocyanate method
-
The invention discloses an alkali-free green synthetic method for isothiocyanate, and relates to the field of organic chemical industry. The method includes the steps: (1) adding solvents into carbon sulfide reagents and primary amine serving as raw materials, performing organic reaction at the temperature of 100-150 DEG C for 10-30 hours; (2) cooling and spin-drying the raw materials after reaction, adding dichloromethane, extracting and separating organic phases by 10% of dilute hydrochloride acid, washing the organic phases, combining the organic phases into an organic layer, washing the organic layer with saturated salt water, drying the organic layer by anhydrous Na2SO4, and performing column chromatographic separation to obtain the isothiocyanate. The molar ratio of the carbon sulfide reagents to the primary amine is 1:1.2-3. Compared with a preparation method in the prior art, the method has the advantages that only heating reaction needs to be performed in the solvents, additional alkali is omitted, and the method is greener and more environmentally friendly and has better application values.
- -
-
Paragraph 0024; 0025; 0026; 0042; 0043; 0044; 0051-0053
(2017/08/26)
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- Aminobenzimidazoles and Structural Isomers as Templates for Dual-Acting Butyrylcholinesterase Inhibitors and hCB2R Ligands To Combat Neurodegenerative Disorders
-
A pharmacophore model for butyrylcholinesterase (BChE) inhibitors was applied to a human cannabinoid subtype 2 receptor (hCB2R) agonist and verified it as a first-generation lead for respective dual-acting compounds. The design, synthesis, and pharmacological evaluation of various derivatives led to the identification of aminobenzimidazoles as second-generation leads with micro- or sub-micromolar activities at both targets and excellent selectivity over hCB1and AChE, respectively. Computational studies of the first- and second-generation lead structures by applying molecular dynamics (MD) on the active hCB2R model, along with docking and MD on hBChE, has enabled an explanation of their binding profiles at the protein levels and opened the way for further optimization. Dual-acting compounds with “balanced” affinities and excellent selectivities could be obtained that represent leads for treatment of both cognitive and pathophysiological impairment occurring in neurodegenerative disorders.
- Dolles, Dominik,Nimczick, Martin,Scheiner, Matthias,Ramler, Jacqueline,Stadtmüller, Patricia,Sawatzky, Edgar,Drakopoulos, Antonios,Sotriffer, Christoph,Wittmann, Hans-Joachim,Strasser, Andrea,Decker, Michael
-
supporting information
p. 1270 - 1283
(2016/07/27)
-
- A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates
-
A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.
- He, Yimiao,Li, Jing,Luo, Shuang,Huang, Jinbo,Zhu, Qiang
-
supporting information
p. 8444 - 8447
(2016/07/07)
-
- Design, synthesis and in vitro evaluation of novel ursolic acid derivatives as potential anticancer agents
-
A series of novel ursolic acid (UA) derivatives modified at the C-3 and the C-28 positions were designed and synthesized in an attempt to develop potential antitumor agents. The in vitro cytotoxicity were evaluated against five cancer cell lines (MGC-803, HCT-116, T24, HepG2 and A549 cell lines) and a normal cell (HL-7702) by MTT assay. The screening results indicated that some of these target compounds displayed moderate to high levels of antiproliferative activities compared with ursolic acid and 5-fluorouracil (5-FU), and exhibited much lower cytotoxicity than 5-FU, indicating that the targeted compounds had selective and significant effect on the cell lines. The induction of apoptosis and affects on the cell cycle distribution of compound 6r were investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which revealed that the antitumor activity of 6r was possibly achieved through the induction of cell apoptosis by G1 cell-cycle arrest. Western blot and qRT-PCR (quantitative real-time PCR) experiments demonstrated that compound 6r may induce apoptosis through both of intrinsic and extrinsic apoptosis pathway.
- Hua, Shi-Xian,Huang, Ri-Zhen,Ye, Man-Yi,Pan, Ying-Ming,Yao, Gui-Yang,Zhang, Ye,Wang, Heng-Shan
-
p. 435 - 452
(2015/04/14)
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- Access to a new class of biologically active quinoline based 1,2,4-triazoles
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As an aspect of our ongoing research in search of new antimicrobial armamentarium, a series of 1,2,4-triazol-3-ylthio-acetamides was constructed and in vitro analyzed for their antimicrobial activity against several bacteria and fungi. Aiming to establish an increased potency, the bioassay results were matched to those of 1,3,4-oxadiazoles, utilized previously. Remarkably, 1,2,4-triazoles were found to possess a good spectrum of antifungal potency, which eventually suggested the azole template as an essential pharmacophore to diversify the biological occupations of the attendant molecules. However, it was noticed that the potency of final analogs against each strain placed reliance on the type of substituent present on benzothiazole ring. The structures of final compounds were confirmed with the aid of IR, 1H NMR, 13C NMR spectroscopy and CHN analysis.
- Patel, Rahul V.,Park, Se Won
-
-
- Synthesis, crystal structure and bio-macromolecular interaction studies of pyridine-based thiosemicarbazone and its Ni(ii) and Cu(ii) complexes
-
A new pyridine-based heterocyclic thiosemicarbazone ligand and its Ni(ii) and Cu(ii) complexes have been synthesized and characterized by structural, analytical and spectral methods. The mono-deprotonated anionic form of the ligand coordinates via NNS donor atoms to yield an octahedral Ni(ii) complex and distorted square planar Cu(ii) complex. UV-visible and fluorescence-based spectroscopic techniques revealed that both metal complexes interact with double stranded DNA via intercalation. A comparative assessment indicated that the Ni(ii) complex displayed superior DNA binding. The interaction of these compounds with bovine serum albumin (BSA) suggested that the ligand and its Cu(ii) complex quenched the intrinsic fluorescence of BSA in a static quenching process, whereas for the Ni(ii) complex, fluorescence quenching of BSA was a combination of both static and collision/dynamic quenching processes. The quenching of the fluorescence of BSA is owing to energy transfer from the tryptophan residues of BSA to the compounds bound to BSA. Cytotoxicity tests based on the standard MTT assay revealed that the Cu(ii) complex displayed prominent anti-proliferative activity against HeLa cells.
- Basu, Arghya,Thiyagarajan, Durairaj,Kar, Chirantan,Ramesh, Aiyagari,Das, Gopal
-
p. 14088 - 14098
(2013/08/23)
-
- Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent
-
A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH 3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Liu, Pengfei,Li, Chunyan,Zhang, Jingwei,Xu, Xiaoyong
-
supporting information
p. 3342 - 3351
(2013/10/01)
-
- Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process
-
A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.
- Li, Zheng-Yi,Ma, Hong-Zhao,Han, Chen,Xi, Hai-Tao,Meng, Qi,Chen, Xin,Sun, Xiao-Qiang
-
p. 1667 - 1674
(2013/07/19)
-
- Domino synthesis of novel series of 4-substituted 5-thioxo-1,2,4- triazolidin-3-one derivatives
-
The efficient synthesis of 4-substituted 5-thioxo-1,2,4-triazolidin-3-one derivatives (4-substituted thiourazoles) via domino combination of thiophosgene, aliphatic or aromatic amines, and ethyl carbazate is presented.
- Ghorbani-Choghamarani, Arash,Sardari, Sara
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p. 1078 - 1081
(2013/08/23)
-
- Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2
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An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.
- Jamir, Latonglila,Sinha, Upasana Bora,Nath, Jayashree,Patel, Bhisma K.
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experimental part
p. 951 - 958
(2012/02/01)
-
- New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure-activity relationships
-
A series of novel benzoimidazo and N-aryl-5-oxo-imidazo[1,2-b]isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed.
- Bollini, Mariela,Casal, Juan Jose,Alvarez, Diego E.,Boiani, Lucia,Gonzalez, Mercedes,Cerecetto, Hugo,Bruno, Ana Maria
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experimental part
p. 1437 - 1444
(2009/09/25)
-
- Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts
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We have developed a general economical and environmentally benign method for the preparation of isothiocyanates from the corresponding dilhiocarbamic acid salts by using cheap and readily available reagent molecular iodine. This is perhaps the most efficient method reported so far for the synthesis of isothiocyanates. The reagent is easily available and nontoxic, and the precipitated sulfur can be removed easily; hence, this method is most suitable for large-scale synthesis. Wiley-VCH Verlag GmbH & Co. KGaA.
- Nath, Jayashree,Ghosh, Harisadhan,Yella, Mamesh,Patel, Bhisma K.
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experimental part
p. 1849 - 1851
(2009/08/07)
-
- A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
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An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.
- Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
-
experimental part
p. 1503 - 1506
(2010/05/18)
-
- Diethyl chlorophosphate: A mild and versatile reagent for the one-pot preparation of isothiocyanates from amines
-
A simple, efficient, and new method has been developed for the synthesis of isothiocyanates from amines. The reaction of a variety of aromatic and aliphatic amines with carbon disulfide in the presence of diethyl chlorophosphate as an efficient reagent proceeded effectively to afford the corresponding isothiocyanates in moderate yields. This method is easy, rapid, and moderate-yielding for the synthesis of isothiocyanates from amines. Georg Thieme Verlag Stuttgart.
- Kaboudin, Babak,Jafari, Ehsan
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experimental part
p. 2683 - 2685
(2009/04/04)
-
- 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 3: Synthesis and activity of isosteric analogs
-
Structure-activity relationships and efforts to optimize the pharmacokinetic profile of isosteric analogs of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among those examined, compound 25 showed potent affinity for cannabinoid receptor 1 (CB1) and receptor 2 (CB2). This compound displayed oral bioavailability and analgesic activity.
- Kai, Hiroyuki,Morioka, Yasuhide,Koriyama, Yuji,Okamoto, Kazuya,Hasegawa, Yasushi,Hattori, Maki,Koike, Katsumi,Chiba, Hiroki,Shinohara, Shunji,Iwamoto, Yuka,Takahashi, Kohji,Tanimoto, Norihiko
-
scheme or table
p. 6444 - 6447
(2009/09/30)
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- 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: Orally bioavailable compounds
-
Structure-activity relationships and efforts to optimize the pharmacokinetic profile of a class of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among the compounds examined, compound 14 showed potent affinity and high selectivity for CB2, and compound 23 showed potent affinities against CB1 and CB2. These compounds displayed oral bioavailability.
- Kai, Hiroyuki,Morioka, Yasuhide,Tomida, Minoru,Takahashi, Tadashi,Hattori, Maki,Hanasaki, Kohji,Koike, Katsumi,Chiba, Hiroki,Shinohara, Shunji,Kanemasa, Toshiyuki,Iwamoto, Yuka,Takahashi, Kohji,Yamaguchi, Yoshitaka,Baba, Takahiko,Yoshikawa, Takayoshi,Takenaka, Hideyuki
-
p. 3925 - 3929
(2008/02/11)
-
- 2-NAPHTHYLIMINO-1,3-THIAZINE DERIVATIVE
-
The formula (I): wherein each of R2 and R3 is, same or different, C2-C4 alkyl or the like; or R2 and R3 are taken together with the adjacent carbon atom to form a 5 to 8 membered non-aromatic carbocyclic ring; R4 is C1-C6 alkyl or the like; X is an oxgen atom or a sulfur atom; A is the group of the formula: wherein R1 is, same or different, alkyl or the like; W is C2-C6 alkylene which may contain an optionally substituted heteroatom(s) or the like; n is an integer of 0 to 7, a pharmaceutically acceptable salt, or a solvate thereof.
- -
-
Page/Page column 14-15
(2008/06/13)
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- Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur
-
The direct molybdenum-catalyzed sulfuration of a variety of isonitriles with elemental sulfur or propene sulfide as sulfur donors affords the corresponding isothiocyanates in good yields and under mild reaction conditions. A catalytic cycle is suggested, in which the molybdenum oxo disulfur complex operates as the active sulfur-transferring species. A novel adduct between the isonitrile and the molybdenum complex has been characterized by X-ray analysis and its association constant determined by UV-vis spectroscopy, but this adduct appears not to be involved in the sulfur-transfer process.
- Adam, Waldemar,Bargon, Rainer M.,Bosio, Sara G.,Schenk, Wolfdieter A.,Stalke, Dietmar
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p. 7037 - 7041
(2007/10/03)
-
- Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors
-
The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.
- Wilson, Kenneth J.,Illig, Carl R.,Subasinghe, Nalin,Hoffman, James B.,Jonathan Rudolph,Soll, Richard,Molloy, Christopher J.,Bone, Roger,Green, David,Randall, Troy,Zhang, Marie,Lewandowski, Frank A.,Zhou, Zhao,Sharp, Celia,Maguire, Diane,Grasberger, Bruce,DesJarlais, Renee L.,Spurlino, John
-
p. 915 - 918
(2007/10/03)
-
- THERMOLYSIS AND PHOTOLYSIS OF SOME THIOUREA DERIVATIVES (PART I)
-
Thermolysis od N-benzoyl-N'-phenylthiourea (BPTU) on heating in air at 230 deg C gives NH3, H2S, benzaldehyde, benzil, aniline, azobenzene, benzamide, benzanilide, phenylisothiocyanate, phenylcyanamide, thiocarbanilide and benzoylisothiocyanate, whereas thermolysis of N-benzoyl-N'-benzylthiourea (BBTU) affords NH3, H2S, benzaldehyde, benzil, toluene, bibenzyl, stilbene, benzamide, cyanamide, benzylisothiocyanate, benzoylthiourea and benzoylisothiocyanate.Thermolysis of N-benzoyl-N'-α-naphthylthiourea (BNTU) under the same conditions gives NH3, H2S, benzaldehyde, benzil, benzamide, α-naphthylisothiocyanate, α-naphthanilide, α-naphthylcyanamide, benzoylisothiocyanate, α-naphthylamine and N,N'-di-α,α'-naphthylthiourea.Analogous results were also obtained on photolysis of (BPTU), (BBTU) and (BNTU) with the exception of NH3 and the photodegradation products of phenylthiourea, benzylthiourea and α-naphthylthiourea respectively.The main feature of these pyrolyses is the homolysis of the amide and thioamide bonds providing free radicals that undergo different reactions involving H-abstraction, dimerization, coupling, fragmentation, rearrangement and disproportionation to yield the identified products.
- Aly, M. M.,Fahmy, A. M.,Gaber, A. M.
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p. 253 - 258
(2007/10/02)
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- Novel reactions of S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate
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S,S'-Bis(1-phenyl-1H-5-yl) dithiocarbonate (1) was synthesized in good yield from 1-phenyl-5-mercapto-5H-tetrazole (2) and trichloromethyl chloroformate (TCF).The structure of 1 was confirmed by using X-ray crystal analysis.The reagent (1) could be applied to the formation of amides, Friedel-Crafts type reactions, isothiocyanate syntheses, and carbonyl group insertion reactions.Keywords - S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; X-ray crystal analysis; amide; isothiocyanate; Friedel-Crafts reaction; carbonyl group insertion reaction.
- Takeda, Kazuyoshi,Tsuboyama, Kanoko,Takayanagi, Hiroaki,Shirokami, Rie,Takeura, Masumi,Ogura, Haruo
-
p. 2334 - 2337
(2007/10/02)
-
- DI-2-PYRIDYL THIONOCARBONATE. A NEW REAGENT FOR THE PREPARATION OF ISOTHIOCYANATES AND CARBODIIMIDES.
-
Reaction of amines with di-2-pyridyl thionocarbonate affords the corresponding isothiocyanates at room temperature, while reaction of N,N'-disubstituted thioureas with di-2-pyridyl thionocarbonate in the presence of 4-dimethylaminopyridine as a catalyst affords the corresponding carbodiimides in high yields.
- Kim, Sunggak,Yi, Kyu Yang
-
p. 1661 - 1664
(2007/10/02)
-
- 1H and 13C NMR Studies on 3-Aryl-2-thioxo-4-oxazolidinones and 3-Arylrhodanines
-
3-Aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines have been studied for magnetic non-equivalence of diastereotopically related proton and 13C nuclei in rotational isomers, and for steric interactions between the aryl and heterocyclic moieties of these compounds.For the majority of rotational isomers the barriers to internal rotation about the aryl C-N bond were >100 kJ mol-1, due to the steric bulk of the thiocarbonyl group.Chemical isolation of several of the diastereomers was achieved.The enhanced steric effect and the difference in the electronic effect of the sulphur atom in relation to the oxygen atom appeared to have no influence on the small chemical shift differences of the rotational isomers, detected for some 1H and some 13C nuclei.
- Aksac, Zihni,Pinar, Esat,Icli, Siddik
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p. 548 - 551
(2007/10/02)
-
- Elektrochemische Synthesen, XVIII. Reaktionen des Naphthalinradikalkations mit Nucleophilen
-
Solid naphthalene radical cation hexafluorophosphate at -77 deg C reacts with tetrabutylammonium cyanide, acetate, thiocyanate, and chloride in dichloromethane in up to 38 percent current efficiency referred to the corresponding naphthalene derivatives.
- Fritz, Heinz P.,Ecker, Peter
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p. 3643 - 3654
(2007/10/02)
-
