Design, synthesis, and antimicrobial activity of some novel homodrimane sesquiterpenoids with diazine skeleton

Kuchkova, K. I.; Aricu, Aculina; Secara, Elena; Barba, Alic; Vlad, P. F.; Ungur, Nicon; Tuchiluş, Cristina; Shova, Sergiu; Zbancioc, Gheorghiță; Mangalagiu, Ionel I.

doi:10.1007/s00044-013-0720-3

Cited by 25 publications

(16 citation statements)

References 32 publications

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“…The geometries of this fragment in the two symmetrically independent molecules were similar and also similar to those found in other related compounds [9,[11][12][13][14][15]. A superposition of molecules A and B that was produced by shifting the least-squares positions of C2, C4, C7, and C9 showed that their conformations differed by the different C9-C11-C12-O1 torsion angles in them.…”

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confidence: 82%

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Synthesis and Structure of Homodrimane Sesquiterpenoids Containing 1,2,4-Triazole and Carbazole Rings

et al. 2015

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confidence: 82%

“…Starting ' 8,13 -bicyclohomofarnesoic acid (3) for synthesizing amides 1 and 2 was synthesized from norambreinolide (4) in overall yield 60%, as reported [9]. The key step in the six-step synthesis was oxidation of ' 8,13 -bicyclohomofarnesen-12-ol (5) by Jones reagent.…”

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confidence: 99%

Synthesis and Structure of Homodrimane Sesquiterpenoids Containing 1,2,4-Triazole and Carbazole Rings

et al. 2015

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“…2-((5-(Amino(piperidin-1-yl)methylene)-6-oxo-2-thioxo-1,2,5,6-tetrahydropyrimidin-4-yl)methyl)isoindoline-1,3-dione (14) Sixty (10 5 colony forming unit (CFU)/mL) was distributed on the surface of the agar plates using a sterile glass spreader, whereas for the antifungal assay a loopful of a particular fungal isolate was transferred to 3 mL sterile saline to get a suspension of the corresponding species; 0.1 mL of the spore suspension was distributed on the surface of sterile Sabouraud dextrose agar plates. Six millimeter diameter wells were punched in the agar media and filled with 100 µL of the tested chemical compound (500 µg/mL in DMSO) which is previously sterilized through 0.45 sterile membrane filter.…”

Section: Reaction Of Compound 3 With Ethanolic Naohmentioning

confidence: 99%

“…11) Recently, they are evaluated as anti-Alzheimer's agents. 12) Moreover, the biological activities of 1,2,4-triazoles, 13) 1,3-diazines, 14) 1,3-oxazines, 15) thioureas 16) are well known.…”

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confidence: 99%

Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment

Hemdan

El‐Sayed

2016

Chem. Pharm. Bull.

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Phthalimidoacetyl isothiocyanate underwent addition-cyclization reactions with some nitrogen and carbon nucleophilic reagents. Simultaneous or subsequent cyclization of the obtained adducts gave target heterocyclic systems such as 1,2,4-triazoles, 1,3-diazines, 1,3-oxazines and thiourea attached to a phthalimido moiety. The antimicrobial activity of the synthesized compounds was tested.Key words phthalimidoacetyl isothiocyanate; 1,2,4-triazol; 1,3-diazine; 1,3-oxazine; thiourea; antimicrobial are well known.In the past few years the authors have been involved in the uses of aroyl isothiocyanates [17][18][19][20] and acyl isothiocyanates [21][22][23][24] in different synthetic strategies of target heterocycles. Studies on the chemistry of aroyl and/or acyl isothiocyanates have established the value of these compounds as starting materials in the synthesis of a wide variety of heterocyclic systems and thiourea derivatives. [17][18][19][20][21][22][23][24][25][26][27] Based on the previous work, we have been synthesized variety of heterocyclic systems bearing phthalimido moiety by using 2-phthalimidobenzoyl isothiocyanate 19) and phthalimidoacyl isothiocyanate.22) In the current study, a further stage reactions of phthalimidoacetyl isothiocyanate was performed. Results and DiscussionTreatment of a solution of phthalimidoacetyl isothiocyanate 1 in a dry acetonitrile with 2-cyanoacetohydrazide at room temperature gave thiosemicarbazide derivative 2 in a good yield. On the other hand, the reaction of a mixture of isothiocyanate 1 and 2-cyanoacetohydrazide in acetonitrile under refluxing conditions produced 1,2,4-triazole derivative 3 in one pot-reaction. However, boiling a solution of the adduct 2 in acetonitrile also gave the 1,2,4-triazole derivative 3. Refluxing of compound 3 in ethanolic-hydrochloric acid mixture afforded ester derivative 4. On the other hand, when a solution of 3 in ethanol was boiled with a catalytic amount of sodium hydroxide, followed by acidification with dilute HCl furnished a carboxylic acid derivative 6 as illustrated in Chart 1.The structures of the synthesized compounds 2-4 and 6 were elucidated from their microanalytical and spectral data. Thus, their IR spectra displayed bands corresponding to NH, CO and C=S, as well as stretching band of CN group for compounds 2 and 3. The 1 H-NMR spectra of the synthesized compounds are in accord with their proposed structures as they showed signals for aromatic protons and aliphatic protons in addition to NH protons in the downfield region exchangeable with D 2 O. The appearance of an exchangeable broad singlet signal for compound 4, at δ: 7.16 ppm corresponds to SH proton suggests its existence entirely as aromatic triazole structure. The relatively high δ value of SH proton suggests chelation shown (Chart 1). The 1 H-NMR spectrum of compound 6 showed the absence of a signal corresponding to CH 2 protons in the up field region, instead it revealed two olefinic signals at δ: 5.88 and 5.94 ppm integrated to one proton. These observations suggest that...

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“…In a search for new biologically active compounds and in continuation of our group's investigations of obtaining nitrogen-containing sesquiterpenoids [2][3][4][5], in the present paper the synthesis of new drimane and homodrimane lactams by the Beckmann rearrangement of some ketoximes is described.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Drimane and Homodrimane Lactams by Beckmann Rearrangement of Some Ketoximes

Secara¹

2016

ChemJMold

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Design, synthesis, and antimicrobial activity of some novel homodrimane sesquiterpenoids with diazine skeleton

Cited by 25 publications

References 32 publications

Synthesis and Structure of Homodrimane Sesquiterpenoids Containing 1,2,4-Triazole and Carbazole Rings

Synthesis and Structure of Homodrimane Sesquiterpenoids Containing 1,2,4-Triazole and Carbazole Rings

Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment

Synthesis of New Drimane and Homodrimane Lactams by Beckmann Rearrangement of Some Ketoximes

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