- Synthesis and antiproliferative evaluation of novel steroid-benzisoselenazolone hybrids
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The two different types of steroidal benzisoselenazolone hybrids were synthesized by incorporating benzisoselenazolone scaffold into dehydroepiandrosterone and B-norcholesterol. The antiproliferative activity of the synthesized compounds against some carcinoma cell lines were investigated. The results showed that some of these compounds have better inhibitory activity than abiraterone on the proliferation of tumor cells associated with human growth hormone, and have less cytotoxicity on normal human cells. In particular, the IC50 values of the compound 8a and 8f are 5.4 and 6.5 μmol/L against human ovarian carcinoma (SKOV3) cell line, and possess SI values of 13.9 and 10.5, respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.
- Cui, Jianguo,Wei, Meizhen,Pang, Liping,Gan, Chunfang,Xiao, Junan,Shi, Haixin,Zhan, Junyan,Liu, Zhiping,Huang, Yanmin
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- Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives
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Sixty-one novel steroidal imidazolium salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin?imidazolium salt derivatives displayed much higher cytotoxic activities than choles
- Deng, Guogang,Zhou, Bei,Wang, Jing,Chen, Zhuo,Gong, Liang,Gong, Yaxiao,Wu, Dongmei,Li, Yan,Zhang, Hongbin,Yang, Xiaodong
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supporting information
p. 232 - 252
(2019/02/28)
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- Sensitized Aliphatic Fluorination Directed by Terpenoidal Enones: A "visible Light" Approach
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In our continued effort to address the challenges of selective sp3 C-H fluorination on complex molecules, we report a sensitized aliphatic fluorination directed by terpenoidal enones using catalytic benzil and visible light (white LEDs). This sensitized approach is mild, simple to set up, and an economical alternative to our previous protocol based on direct excitation using UV light in a specialized apparatus. Additionally, the amenability of this protocol to photochemical flow conditions and preliminary evidence for electron-transfer processes are highlighted.
- Bume, Desta Doro,Harry, Stefan Andrew,Pitts, Cody Ross,Lectka, Thomas
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p. 1565 - 1575
(2018/02/09)
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- 17 beta-imidazolidinyl bromide-dehydroepiandrostane derivative and preparation method and application thereof
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The invention provides a 17 beta- imidazolidinyl bromide-dehydroepiandrostane derivative which has the good pharmacological activity and can be applied to preparation of anti-tumor drugs. Based on theembodiment result, the obtained 17 beta-imidazolidinyl
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Paragraph 0113; 0114
(2019/01/14)
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- Efficient syntheses of 17-β-amino steroids
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17β-Amino steroids such as 17β-amino-1,3,5(10)-estratrien-3-ol (1), 17β-amino-5α-androstan-3β-ol (2) and, 17β-amino- 3β-hydroxyandrost-5-ene (3) have been widely used as a key intermediates in the synthesis of a variety of biologically active steroid derivatives though concise, high yielding syntheses of these compounds has yet to be reported. 17β-Amino-1,3,5(10)-estratrien-3-ol (1) and 17β-amino-5α- androstan-3β-ol (2) were prepared in high yield by reductive amination of estrone and epiandrosterone using benzylamine and sodium triacetoxyborohydride followed by catalytic hydrogenolysis of the resulting 17β-benzylamino derivatives. Attempts to prepare 17β-amino-3β-hydroxyandrost-5-ene (3) from dehydroepiandosterone using a similar approach resulted in partial reduction of the double bond. 17β-Amino-3β-hydroxyandrost-5-ene (3) was ultimately obtained in high yield by reductive amination of dehydroepiandosterone using allylamine and sodium triacetoxyborohydride followed by removal of the allyl group from the resulting 17β-allylamino derivative with dimethylbarbituric acid and Pd(PPh3)4 as catalyst.
- Taylor, Scott D.,Harris, Jesse
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scheme or table
p. 1098 - 1102
(2011/08/22)
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- NOVEL METHOD FOR THE DIASTEREOSELECTIVE PRODUCTION OF A CHIRAL PRIMARY AMINE ON A STEROID
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The invention relates to a diastereoselective method for obtaining a primary amine on a steroid, comprising the reduction of an oxime by lithium in ammonia at a low temperature in an ether/alcohol mixture.
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Page/Page column 5
(2010/04/23)
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- Steroids, LIII: New Routes to Aminosteroids [1]
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Steroid ketoximes were reduced with sodium tetrahydroborate in the presence of nickel chloride or molybdenum trioxide. These processes yielded 17α- and 20α- aminosteroids (1c-5c) in higher yields than common reduction methods.
- Szendi,Dombi,Vincze
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p. 1189 - 1196
(2007/10/03)
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- Steroids and Related Studies: Part 82 - Chandonium Related Azasteroidal Neuromuscular Blockers
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Modelled on clinically active chandonium iodide (1) different azasteroidal neuromuscular blockers have been designed. 17β-Dimethylamino-3β-pyrrolidino-5-androstene dimethiodide (HS-854) (2), having not the 17a-aza-D-homo system but extranuclear quaternary ammonium head with nearly equivalent steric placement, and the 17β-dimethylamino-3α-pyrrolidino-5-androstene dimethiodide (HS-1046) (dimethiodide of 6) have been synthesized. 17β-Dimethylamino-3β-pyrrolidino-5α-androstane dimethiodide (HS-944) (7) is the dihydro analogue of HS-854 (2).The other modification, viz 6-hydroxymethyl-17β-dimethylamino-3β-pyrrolidino-5-androstene dimethiodide (HS-892) (13) has a sterically significant substituent at position-6 which should also alter hydrophilic-lipophilic balance.All the new bisquaternary steroids are active as neuromuscular blockers in the rat phrenic nerve diaphragm preparation.The structure-activity relationship has been discussed.
- Singh, Harkishan,Gupta, Rakesh Kumar,Bhardwaj, Tilak Raj
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p. 508 - 512
(2007/10/02)
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- SYNTHESIS OF 16α-BROMOACETOXY ANDROGENS AND 17β-BROMOACETYLAMINO-4-ANDROSTEN-3-ONE: POTENTIAL AFFINITY LABELS OF HUMAN PLACENTAL ARMATASE.
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A novel synthesis of 16α-hydroxy-4-androstene-3,17-dione (3), 16α-hydroxy-4-androstene-3,6,17-trione (4), 17β-amino-5-androsten-3β-ol (10) and 17β-amino-4-androsten-3-one (14) is described. 16α-Bromoacetoxy-4-androstene-3,17-dione (5), 16α-bromoacetoxy-4-androstene-3,6,17-trione (6) and 17β-bromoacetylamino-4-androsten-3-one (15) were synthesized as potentially selective irreversible inhibitors of androgen aromatases. 16α-Bromo-4-androstene-3,17-dione (1) and 16α-bromo-4-androstene-3,6,17-trione (2) were converted to compounds 3 and 4 in 80-90percent yield by controlled stereospecific hydrolysis using sodium hydroxide in aqueous pyridine.Reductive amination of 3β-hydroxy-5-androsten-17-one and 3-methoxy-3,5-androstadien-17-one (11) using ammonium acetate and sodium cyanohydridoborate (NaBH3CN) and a subsequent treatment with acid gave the amines 10 and 14, respectively, as a salt.The corresponding 17-imino compounds 9 and 13 were also isolated from the reaction mixtures when methanol was used as a solvent for the reaction.The 16α-hydroxyl compounds 3 and 4 and the 17β-amino compound 14 were converted to the corresponding bromoacetyl derivatives, 5, 6, and 15, with bromoacetic acid and N,N'-dicyclohexylcarbodiimide.
- Numazawa, Mitsuteru,Osawa, Yoshio
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p. 149 - 160
(2007/10/02)
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