Totally synthetic steroid hormones—XX

Stein, R.P.; Buzby, G. C.; Smith, Heather

doi:10.1016/s0040-4020(01)92768-1

Cited by 20 publications

(5 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was initially isolated from the urine of a pregnant mare (Girard et at., 1932), and was initially synthesized by Bagli et al (1964) using the spores of Nocardia restrictus. It was later synthesized chemically by Stein et al (1969). Recently, it has been shown to be an inhibitor of the conversion of 173-estrone to 17fl-estradiol by human type 1 17fl-hydroxysteroid dehydrogenase (17fl-HSD1), a key enzyme in the biosynthesis of 17flestradiol from estrone in human breast tissues (Sawicki et al, 1999).…”

Section: Commentmentioning

confidence: 99%

Equilin

Sawicki¹,

Li²,

Ghosh³

1999

Acta Crystallogr C

View full text Add to dashboard Cite

3-Hydroxyestra-1,3,5(10),7-tetraen-17-one, C18H20O2, crystallizes in space group P2(1)2(1)2(1) from ethyl acetate. The planarity of the B ring, and the difference in puckering of the C and D rings from that of estrone, are due to the presence of the C7 = C8 double bond, which may explain its function as an inhibitor of human type 1 17 beta-hydroxysteroid dehydrogenase, instead of being its substrate.

show abstract

Section: Commentmentioning

confidence: 99%

Equilin

Sawicki¹,

Li²,

Ghosh³

1999

Acta Crystallogr C

View full text Add to dashboard Cite

show abstract

“…Under reductive conditions (NHJMeOH), 13 gave the corresponding allylic alcohol 16. The 8cr -OH configuration was assigned to 16 by comparison of its 'H-NMR spectra to that of a sample synthetized independently by epoxidation of 6 followed by acid ring opening as described by Stein et al [12]. Since the hydroperoxide reduction to an alcohol (13-+16) does not involve the C-0 bond, the same 8a -0OH configuration was assigned to 13.…”

Section: Dye-sensitized Photo-oxygenation Of the Estratetraene Derivamentioning

confidence: 99%

“…The X-ray-determined and calculated stable conformation of l b (Table 3, Fig. 2c) has a half-chair conformation for ring C where two allylic H-atoms, H,-C (12) and H-C (8), are quasiorthogonal to the olefinic n-system plane. This geometry would predict some extend of ene-type reaction, which, however, was not observed (only seco-aldehyde 3 was detected and isolated).…”

Section: Geometric Factorsmentioning

confidence: 99%

See 1 more Smart Citation

Photo‐oxygenation of Styrenic Estrogens: Structural Analysis of 8,9‐Didehydro‐, 6,7‐Didehydro‐, and 9,11‐Didehydroestrone Derivatives and Their Reactivity towards Singlet Oxygen

Malet

Planas

Brosa

et al. 1991

Helvetica Chimica Acta

View full text Add to dashboard Cite

Dedicated to Prof. Dr. Kurt Schuffner on the occasion of his 60th birthday ( . V111.91)A series of didehydro-3-0 -methyl-estrones having a styrenic framework, with the ring-A-conjugated double bond in all three possible positions (8,9-didehydro-(6), 9,1 I-didehydro-(lb), 6,7-didehydro-(9), and the 12,18-dinor-8,9-didehydroestrone analog 1 l), were compared for their reactivity towards singlet oxygen. Under dye-sensitized photo-oxygenation conditions, both, products derived from ene-type reactions with the isolation of a stable hydroperoxide and a fragmentation product, were obtained from 6 (see Scheme 3 ) , while only fragmentation took place for l b (Scheme I ) . Kinetic studies indicated that 6 is more reactive towards '0, than l b (B = 9.2.mol. I-' us 3.3. lo-' mol.I-', resp.). The observed reactivity, apparently, does not match with ene-type reaction and [2 + 2]cycloaddition being in competition, since the most activated substrate 6 preferentially yields ene-type products and their derivatives. Conformational analysis on the structure of 6 and lb, both calculated by molecularmechanic techniques (MMPMI) and determined by X-ray diffraction, show that the allylic H-atoms satisfy the orthogonality rule for ene-type reactions. The product distribution is best rationalized by applying Fukui's rule which takes into account a combination of electronic and geometric factors. Substrates 9 and 11 yielded photoproducts arising from ene-type reaction with no stable primary products isolated (Scheme 4 ) . Geometric considerations based on the calculated structures by molecular mechanics are consistent with the observed results.

show abstract

“…The Wyeth group also reported the ready conversion of 14 (and derivatives thereof) into the methyl ethers of equilenin and equilin (21) [23]. Epoxidation of the A 8 -unsaturation of 14 followed by acid-catalyzed rearrangement gave a good yield of 8a-hydroxy-17.…”

Section: Scheme 8-1mentioning

confidence: 99%

A + D → Ad → Abcd

1974

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

Totally synthetic steroid hormones—XX

Cited by 20 publications

References 33 publications

Equilin

Equilin

Photo‐oxygenation of Styrenic Estrogens: Structural Analysis of 8,9‐Didehydro‐, 6,7‐Didehydro‐, and 9,11‐Didehydroestrone Derivatives and Their Reactivity towards Singlet Oxygen

A + D → Ad → Abcd

Contact Info

Product

Resources

About