Thiocyanato Derivatives Research Articles

Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

AbstractFacile and efficient syntheses of 4‐(1H‐pyrrol‐1‐yl)‐coumarins and 6‐(1H‐pyrrol‐1‐yl)‐coumarins from the corresponding aminocoumarins are reported. The transformations were optimized and their corresponding scope and limitations were assessed. Selected (1H‐pyrrol‐1‐yl)‐coumarins were further subjected to a mild thiocyanation, undergoing selective functionalization on the pyrrole nucleus. A set of 10 differently substituted compounds was submitted to activity testing against various fungal strains. It was found that the introduction of a SCN moiety increased the antifungal activity, turning some compounds into fungicidal agents, to the point that one of the thiocyanato derivatives displayed an antifungal profile comparable to those of fluconazole and nystatin.

ChemInform Abstract: Metal‐Free Thiocyanation of Imidazoheterocycles Through Visible Light Photoredox Catalysis.

AbstractThe title reaction is applied to the parent compound (Ia) and a series of substituted analogues to produce the desired C‐3 thiocyanato derivatives under ambient air at room temperature.

Synthesis and Anti-Actinomycotic Activity of the Oligomycin A Thiocyanato Derivative Modified at 2-Oxypropyl Side Chain

Synthesis and Anti-Actinomycotic Activity of the Oligomycin A Thiocyanato Derivative Modified at 2-Oxypropyl Side Chain

ChemInform Abstract: Reactions of Thiocyanato Derivatives of Phenothiazine with Dialkyl/ Dithiophosphates.

ChemInform Abstract: Reactions of Thiocyanato Derivatives of Phenothiazine with Dialkyl/ Dithiophosphates.

Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives

Novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazoles (3a-f) were synthesized from benzisoxazolyl-3-acetic acid and thiosemicarbazide. Reaction of 3 with bromine in glacial acetic acid in the presence of anhydrous sodium acetate yielded the corresponding 5-bromo derivatives (4a-f). While compound 3 furnished the 5-nitroso derivatives (5a-f) on refluxing with sodium nitrite solution. Thiocyanato derivatives (6a-f) were obtained by treating the imidazothiadiazole 3 with bromine and potassium thiocyanate in glacial acetic acid at room temperature. The structures of the newly synthesized compounds were confirmed by IR, NMR, mass and elemental analysis. All the compounds were screened for their antibacterial and antifungal activities. Some of the compounds displayed very good antibacterial and antifungal activity.

Synthesis of sulfide-and disulfide-type bisaporphines from thebaine

The rearrangement reaction of thebaine (1) with methanesulfonic acid, in the presence of hydrogen sulfide, resulted in a sulfide-type bisaporphine 13, instead of the expected thiol 12. The acidic hydrolysis of the thiocyanato derivatives 3, 9, 20 and 21, obtained from thebaine (1), as well as the reduction of 9 and 21 with sodium borohydride yielded disulfide-type bisaporphines 16 and 23.

Crystal structures of two isomeric oximes. (EE)-2-methyl-3-phenyl-3-thiocyanatopropenaldoxime and (Z)-5-methyl-6-phenyl-1,3-thiazin-2-one oxime

The crystal structure of two isomeric oximes, C11N10N2OS have been studied by X-ray diffraction. The open-chain thiocyanato derivative is somewhat'less dense and crystallizes with the orthorhombic space group Pbcn;a,b,c=18.718(1), 10.601(3), 11.528(1) A,Z=8. The heterocyclic isomer occurs as pseudo-orthorhombic (Cmma)twinned crystals of space group P21/n, a, b, c, β=12.11(1), 7.46(1), 12.12(1) A, 100.09(1)o,Z=4. Twinning occurs as a result of the near-equality of the monoclinica andc cell constants.

ChemInform Abstract: Reaction of Dicyano Epoxides with Thiocyanate Ion: Route to α‐ Thiocyanato Derivatives or to 2‐Acetylimino‐1,3‐oxathioles and X‐Ray Crystal Structure of 2‐Acetylimino‐4‐(4‐tolyl)‐1,3‐oxathiole‐5‐ carbonitrile.

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Macrocyclic dimanganese complexes with 1,1 bridging ligands; X-ray crystallographic structure determination of an N-only bridged thiocyanato derivative

X-Ray crystallographic structure determination confirms the inference from i.r. spectra that the µ 1,1 NCS bridge is present in dimanganese(II) complexes of a 22-membered N6 macrocycle: these complexes show no appreciable magetic interaction above 93 K, unlike the µ-methoxo-dimanganese(III) complex of the same ligand.

ChemInform Abstract: Nitriles in Heterocyclic Synthesis: A New Approach for the Synthesis of Thiazole Derivatives.

The reaction of 4-bromo-3-oxo-butyranilide (1) with KSCN afforded the thiocyanato derivative 2. 2-Dicyanomethylthiazol-4-yl-acetanilide (3) was synthesised by reaction of 2 with malononitrile. A variety of substituted thiazol-2-yl malononitriles were prepared by reaction of 3 with hydroxylamine hydrochloride, phenylhydrazine and cinnamonitrile derivatives. The structure assignments of the new compounds are based mainly on 13C and 1H-n.m.r. spectroscopic data.

Nitriles in heterocyclic synthesis: A new approach for the Synthesis of Thiazole derivatives

AbstractThe reaction of 4‐bromo‐3‐oxo‐butyranilide (1) with KSCN afforded the thiocyanato derivative 2. 2‐Dicyanomethylthiazol‐4‐yl‐acetanilide (3) was synthesised by reaction of 2 with malononitrile. A variety of substituted thiazol‐2‐yl malononitriles were prepared by reaction of 3 with hydroxylamine hydrochloride, phenylhydrazine and cinnamonitrile derivatives. The structure assignments of the new compounds are based mainly on 13C and 1H‐n.m.r. spectroscopic data.

Nitrosyl Rhenium Complexes: Thiocyanato Derivatives

AbstractFusion of K2[Re(NO)Cl5] with KSCN produces the ion [Re(NO)(SCN)5]2− which has been isolated as free acid and K+, Na+, NMe4+, Pb2+, Hg2+, phen H+ and dipyH+ salts. A salt of composition Hg2[Re(NO)(SCN)7] has also been prepared. The species [Re(NO)Cl(SCN)4]2− has been obtained from the reaction of H2[Re(NO)(SCN)5] with HCl in aqueous medium and its NMe4+ salt has been isolated. Hydrated Re(NO)Cl3 reacts with KSCN in aqueous medium to produce the ion [Re(NO)Cl2(SCN)3]2− which has been isolated as its phenH+ and dipyH+ salts. The complexes have been characterized through elemental analyses, spectral (u.v., vis., i.r.) properties, magnetic and conductance data. The structures of all those compounds have been proposed.

ChemInform Abstract: STUDY OF THIOCYANATO DERIVATIVES OF THE DECAHYDRODECABORATE(2‐) ION

Chemischer InformationsdienstVolume 14, Issue 43 Organoelement Compounds ChemInform Abstract: STUDY OF THIOCYANATO DERIVATIVES OF THE DECAHYDRODECABORATE(2-) ION H. MONGEOT, H. MONGEOTSearch for more papers by this authorJ. ATCHEKZAI, J. ATCHEKZAISearch for more papers by this author H. MONGEOT, H. MONGEOTSearch for more papers by this authorJ. ATCHEKZAI, J. ATCHEKZAISearch for more papers by this author First published: October 25, 1983 https://doi.org/10.1002/chin.198343264Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume14, Issue43October 25, 1983 RelatedInformation

Trans-chelation in transition metal complexes: Synthesis and characterization of platinum(II) complexes of bis(disphenylarsino)alkanes

Cis and trans complexes of the type Pt(ligand)Cl 2 (ligand = Ph 2As(CH 2) nAsPh 2, n = 6–12, 16) have been synthesized, together with the bromo, iodo and thiocyanato derivatives for n = 10 and 12. The cis complexes are essentially dimeric. The complexes have been characterized by elemental analyses, infrared and proton NMR spectroscopy, solid state reflectance and visible/UV spectroscopy and vapor phase osmometry. Formation of the cis or trans isomer for the complexes Pt(ligand)Cl 2 is critically dependent on the choice of complex precursor: potassium tetrachloroplatinate(II) yields the cis isomer, whilst Zeise's salt gives the trans isomer. The bromo, iodo and thiocyanato derivatives prepared via an exchange reaction give cis complexes. Evidence is presented for the existence of PtNCS and PtSCN linkages both in the solid state and in solution for the thiocyanato derivatives. Product distribution and stereochemistry in all of the complexes are discussed in terms of the factors governing trans chelation.

Organostibines as ligands. Synthesis of dimethyl(α-picolyl)stibine, dimethyl(8-quinolyl)stibine, and ( R; S)-methylphenyl(8-quinolyl)stibine and some transition metal derivatives

The unsymmetrical mono-tertiary stibines dimethyl(α-picolyl)stibine (picstib), dimethyl(8-quinolyl)stibine (quinstib), and ( R; S)-methylphenyl(8-quinolyl)stibine ( R; S-quinstib) have been synthesised and the square-planar complexes [MX 2(picstib)], [MX 2(quinstib)] (where M = Pd or Pt and X = Cl, Br, I or SCN) and [MCl 2( R; S-quinstib)] (where M = Pd or Pt) isolated. The thiocyanato derivatives display linkage isomerism. The octahedral complexes [M(CO) 4-(picstib)] and [M(CO) 4(quinstib)] have also been prepared from the metal hexacarbonyls and the appropriate ligands by UV irradiation in tetrahydrofuran.

ChemInform Abstract: SYNTHESIS AND STUDY OF SOME THIOCYANATO DERIVATIVES OF PLATINUM(II) CONTAINING CYCLOHEXYLISONITRILE

Chemischer InformationsdienstVolume 10, Issue 4 Organoelement Compounds ChemInform Abstract: SYNTHESIS AND STUDY OF SOME THIOCYANATO DERIVATIVES OF PLATINUM(II) CONTAINING CYCLOHEXYLISONITRILE YU. N. KUKUSHKIN, YU. N. KUKUSHKINSearch for more papers by this authorL. V. VRUBLEVSKAYA, L. V. VRUBLEVSKAYASearch for more papers by this authorT. S. ISACHKINA, T. S. ISACHKINASearch for more papers by this authorS. I. BAKHIREVA, S. I. BAKHIREVASearch for more papers by this author YU. N. KUKUSHKIN, YU. N. KUKUSHKINSearch for more papers by this authorL. V. VRUBLEVSKAYA, L. V. VRUBLEVSKAYASearch for more papers by this authorT. S. ISACHKINA, T. S. ISACHKINASearch for more papers by this authorS. I. BAKHIREVA, S. I. BAKHIREVASearch for more papers by this author First published: January 23, 1979 https://doi.org/10.1002/chin.197904279AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume10, Issue4January 23, 1979 RelatedInformation

Novel synthesis of isothiocyanatophosphoranes and isothiocyanatophosphonium salts via ligand substitution. Versatile reagents for converting hydroxy groups into thiocyanate and isothiocyanate functions

Alkoxy- or acyloxy-isothiocyanatophosphoranes (7) and phosphonium salts (12), prepared under mild conditions by stepwise ligand substitution from (5) and (11), respectively, decompose in excellent yield into the corresponding thiocyanato (9) and isothiocyanato (10) derivatives, thus providing a new method of synthesis of (9) and (10).

Antiviral activity of 5-thiocyanatopyrimidine nucleosides

The antiviral activity of the 5-thiocyanatopyrimidine nucleosides 5-NCSrU ∗ ∗ Abbreviations: 5-NCSrU, 5-thiocyanatouridine; 5-NCSdU, 5-thiocyanato-2'-deoxyuridine: 5-NCSaraU, 5-thiocyanato uracil arabinoside or 1-β- d-arabinofuranosyl-5-thiocyanatouracil; tri-O'-acetyl-5-NCSrU, 2',3',5'-tri- O-acetyl-5-thiocyanatouridine; ara-C, cytosine arabinoside, 1-β- d-arabinofuranosylcytosine; 5-ethyl-dU, 5-ethyl-2'-deoxyuridine; dT, 2'-deoxythymidine; 5-IdU, 5-iodo-2'-deoxyuridine; CCID 50, cell culture infecting dose 50 (dose infecting 50% of the cell cultures); PFU, plaque forming units. , 5-NCSdU, 5-NCSaraU and tri- O′-acetyl-5-NCSrU has been evaluated in primary rabbit kidney (PRK) cell cultures challenged with either DNA (vaccinia, herpes simplex) or RNA (vesicular stomatitis) viruses. 5-NCSdU inhibited vaccinia virus multiplication at 10 μg/ml, and vaccinia and herpes simplex virus induced cytopathogenicity at 4 μg/ml. Tri- O′-acetyl-5-NCSrU inhibited vesicular stomatitis virus-induced cytopathogenicity at 1–10 μg/ml. None of the compounds had profound effects on host cell RNA or DNA synthesis, even at 200 μg/ml, as monitored by [ 3H]uridine and [ 3H]thymidine incorporation respectively, except 5-NCSdU, which brought about a 10–30-fold increase of [ 3H]thymidine incorporation at 200 μg/ml. The inhibitory effect of 5-NCSdU on vaccinia virus replication and its stimulatory effect on [ 3H]thymidine incorporation were almost completely reversed by thymidine at concentrations 100 times lower than that of the thiocyanato derivative. When treated with dithiothreitol, the 5-thiocyanatopyrimidine nucleosides also lost a significant part of their biological activity, presumably due to reduction to the corresponding 5-mercapto analogs.

Subunit location of sulfhydryl groups of myosin labeled with a purine disulfide analog of adenosine triphosphate.

A purine disulfide analog of ATP, 6,6'-dithiobis(inosinyl imidodiphosphate), forms mixed disulfides with cysteine residues at what are believed to be ATP regulatory sites of myosin. Blocking these sites causes inactivation of the ATPase activity at the active sites. Two cysteine residues per head are specifically modifed by this disulfide analog. The thiopurine nucleotides can be stoichiometrically displaced from myosin by [14-C]cyanide to give a more stable thiocyanato derivative of the enzyme. [14-C]Thiocyanatomyosin (3.7 14-CN/myosin) was dissociated in 4 M urea and the individual subunits were isolated. The heavy chains each had 0.78 14-CN bound per 200,000 molecular weight unit. The light chain with molecular weight of 20,700 had 1.00 14-CN bound and the 16,500 molecular weight light chain had 0.65 14-CN bound. The two 19,000 molecular weight light chains were not labeled. The two labeled light chains have only a single cysteine which is stoichiometrically modified. These two light chains show a high degree of homology and presumably perform identical functions in myosin. Their specific modification by the purine disulfide analog and their other known properties suggest that they contribute directly to the ATP regulatory sites and may, in fact, function as regulatory subunits.

Reaction of cyclooctatetraenyldipotassium with disulfides and thiocyanato derivatives of the thiophene series

In contrast to organometallic compounds of the phenyllithium type, cyclooctatetraenyldipotassium on reaction with disulfides and thiocyanato derivatives of the thiophene series in tetrahydrofuran does not give thio ethers but enters into an electron-transfer reaction and is converted to cyclooctatetraene. Thiophene derivatives form the potassium salts of the corresponding thiols. When insufficient amounts of cyclooctatetraenyldipotassium are present, thiocyanatothiophenes are converted to disulfides. It is shown that the latter can be obtained as a result of the reaction of thienyl mercaptides with thiocyanatothiophenes.