10. Steroids and related compounds. Part V. Steroid diosphenols

Petrow, Vladimir; Starling, W. W.

doi:10.1039/jr9400000060

Cited by 10 publications

(12 citation statements)

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“…R , = OC,H, chloride gave 3,5-dinitro-4-hydroxy-6-methoxy-2-styrylquinoline (Id), which upon reaction with phosphorus oxychloride gave the 4-chloro derivative Ie. When Ic was allowed to condense with 2aminophenol or 2-amin0-4-chloropheno1, the product was either the 2-methoxy-6-methyl-l-nitro-12H-quino[3,4-b] [1,4] benzoxazine (IIIa) or its 10-chloro derivative (IIIb). One can adequately explain the formation of IIIa and IIIb from the condensation of 2-aminophenols with Ic and Ie on the basis of initial formation of intermediate I1 uia hydrochloric acid elimination (Scheme I).…”

Section: Discussionmentioning

confidence: 99%

“…10-Chloro-2-methoxy -1 -nitro-6-methyl-12H-quino [3,4 b]- [1,4]benzoxazine (1IIb)-This compound was prepared by the method used for IIIa from Ic and 2-amino-4-chlorophenol to give IIIb (70%) as yellow needles from ethanol, mp 240-24Z0.…”

Section: Experimental'mentioning

confidence: 99%

“…The preparation of benzoxazine derivatives via the Turpin (1) reaction of 2-aminophenol with picryl chloride has created much interest both from the synthetic and biological points of view (2)(3)(4)(5). Crossley et al (6) prepared a series of phenoxazine derivatives, and their differential tissue staining and tumor growth retardation activity were determined.…”

mentioning

confidence: 99%

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Synthesis of Benzoxazino-and Naphthoxazinoquinoline Derivatives as Possible Antitumor Agents

Nasr

Abbasi

Nabih

1974

Journal of Pharmaceutical Sciences

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Section: Discussionmentioning

confidence: 99%

Section: Experimental'mentioning

confidence: 99%

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Synthesis of Benzoxazino-and Naphthoxazinoquinoline Derivatives as Possible Antitumor Agents

Nasr

Abbasi

Nabih

1974

Journal of Pharmaceutical Sciences

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“…The contents of the SI include details on the preparation of compounds, [55] and their biological activity [56] as well as the tools used in molecular modeling and computographics. The detailed experimental protocols, spectroscopic and elemental analyses data are provided.…”

Section: Supporting Informationmentioning

confidence: 99%

Stereo‐Electronic, Molecular Connectivity, and Geometric Configuration Approaches towards Designing Antibacterial Agents from 1, 3, 4‐Thiadiazole as the Starting Molecular Template

Yusuf

Khan

et al. 2017

ChemistrySelect

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New 5‐amino‐1,3,4‐thiadiazole‐2‐thiol derivatives have been synthesized based on molecular target designs derived from various molecular descriptors involving configurational geometry, molecular size, and stereoelectronic effects of the desired sub‐structural templates using molecular connectivity design approach. The approach generated fragment‐based pharmacophore sub‐units in comparison to fluoroquinolone template to yield comparable leads with medium molecular size, and nearly flat‐plane molecular geometry framework. The product, namely, 5‐{[‐1‐(4‐chlorophenyl)‐5‐phenyl penta‐2,4‐dien‐1‐ylidene] amino}‐1,3,4‐thiadiazole‐2‐thiol (2 f) showed potent antibacterial activity against both gram‐positive and, gram‐negative strains to validate the design.

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“…spectrum in agreement with the proposed structure; n.m.r. data : 8 0.83 (3-protons singlet, CH,-18); 8 0.88 (6-protons doublet, CH,-26 and CH,-27); 8 1.03 (3-protons singlet, CH,-19); 8 1.15 (3-protons singlet, CH,-2l); 6 2.03 (3-protons singlet, CH,-acetyl); 6 4.63 (1 proton broad signal, H-3); 6 5.38 (I-proton, H-6); the product had spec. act.…”

Section: Cholest-5-ene-3p 20u-diol-20-14c Acetate-3 (Ii)mentioning

confidence: 99%

Synthesis of cholesterol‐20‐¹⁴C

Porto

Gros

1970

J. Labelled Cpd. Radiopharm.

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SUMMARYCholester01-20-~4C was synthesized in four steps from pregneno10ne-20-~~C. The labelled intermediates were proven to be cholest-5-ene-jp, 2Ou-diol acetate-3, cholesta-5, 20 (22)-diene-3/3-01 acetate, and cholesterol acetate by lH-n.m.r. spectroscopical analysis, Chole~teroL20-~~C was obtained with a radiochemical purity exceeding 99 %.In connection with our work on the biosynthesis of bufadienolides from animal and plant origin (l), it was required the preparation of cholestero1 labelled with 14C at any carbon-atom of the side chain but carbons 25, 26 and 27.Since pregnenolone-20-14C had been previously synthesized (2) we chose this labelled steroid as starting material for the preparation of cholesterol labelled with 14C at C-20.When pregnenolone-20-14C acetate (I) was treated with the Grignard reagent prepared from isohexyl bromide (3), cholest-5-ene-3P, 201x-dio1-20-~~C acetate-3 (11) was obtained in good yield. This compound was first synthesized by Petrow and Stuart-Webb (4) although at that time the authors did not disclosed the stereochemistry of the product. The same method was utilized later by Bergman et al. The labelled 20-hydroxy-cholesterol (11), without purification, was dehydrated by reaction with POCl, and pyridine in a sealed tube (') to cholesta-5, 20 (22)-diene-3P-ol-20J4C acetate (111). It seemed reasonable to suppose that * Research Member of the Consejo Nacional de Investigaciones Cientificas y Tknicas-

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10. Steroids and related compounds. Part V. Steroid diosphenols

Cited by 10 publications

References 0 publications

Synthesis of Benzoxazino-and Naphthoxazinoquinoline Derivatives as Possible Antitumor Agents

Synthesis of Benzoxazino-and Naphthoxazinoquinoline Derivatives as Possible Antitumor Agents

Stereo‐Electronic, Molecular Connectivity, and Geometric Configuration Approaches towards Designing Antibacterial Agents from 1, 3, 4‐Thiadiazole as the Starting Molecular Template

Synthesis of cholesterol‐20‐¹⁴C

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10. Steroids and related compounds. Part V. Steroid diosphenols

Cited by 10 publications

References 0 publications

Synthesis of Benzoxazino-and Naphthoxazinoquinoline Derivatives as Possible Antitumor Agents

Synthesis of Benzoxazino-and Naphthoxazinoquinoline Derivatives as Possible Antitumor Agents

Stereo‐Electronic, Molecular Connectivity, and Geometric Configuration Approaches towards Designing Antibacterial Agents from 1, 3, 4‐Thiadiazole as the Starting Molecular Template

Synthesis of cholesterol‐20‐14C

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Synthesis of cholesterol‐20‐¹⁴C