7680-15-1Relevant academic research and scientific papers
Synthesis, Crystal Structure, and Insecticidal Activity of Steroidal N-Piperidone
Ma, Shichuang,Jiang, Weiqi,Hu, Yuxiao,Wang, Qiangping,Wu, Wenjun,Shi, Baojun
, p. 1467 - 1476 (2022/02/10)
A series of steroidal piperidone derivatives were synthesized, and their agricultural activities were evaluated against Myzus persicae, Aphis citricola, Brevicoryne brassicae Linn., and Bemisia tabaci (Gennadius). Most of the tested compounds exhibited potent insecticidal activity against these four pests. Compound I-9 displayed the highest activity against M. persicae, A. citricola, and Brevicoryne brassicae, with LC50 values of 11.3, 10.4, and 8.68 μg/mL, respectively. The mode of action test indicated that these derivatives had superior contact and systemic insecticidal activity against M. persicae. In addition, we initially explored whether the foregut and midgut might be the action sites of the target derivatives against M. persicae. Furthermore, a field trial showed that the control of compound I-9 was similar to that of acetamiprid against M. persicae, at a dose of 50 μg/mL; the control rates were 97.8 and 99.2% after 14 and 21 days, respectively. The structure-activity relationship of these analogues provided some important insights for the discovery and development of new insecticides to solve the current pesticide resistance crisis.
Design, synthesis, brine shrimp lethality and cytotoxicity of some novel 17a-aza-D-homo-androster-17-one derivatives
Hong, Dongfeng,Ma, Yiming,Song, Siyao,Li, Na,Wang, Junru
supporting information, p. 3985 - 3991 (2020/04/27)
In this work, twenty-eight novel 17a-aza-D-homo-androster-17-one derivatives, which divided into two categories, were synthesized with commercial available starting material (dehydroepiandrosterone) via oximation reaction, Beckmann rearrangement, hydroxyl protection, N-alkylation and deprotection. All compounds were characterized by 1H NMR, 13C NMR and HRMS. The structure of 14 g was also identified by X-ray single crystal diffraction. The bioactivities, brine shrimp toxicity and cytotoxicity, of all derivatives were tested. The results indicated that compounds 11 h, 11i, 11 m, 11 s, 14 b and 14 g exhibited excellent toxicity against brine shrimp with LC50 values ranging from 5.34 to 16.89 μg/mL, and compounds 11 s and 14 g displayed significant cytotoxicity against HT29 cells and A549 cells with IC50 values of 9.70 μM and 8.85 μM, respectively. Structure-activity relationships are discussed based on the results obtained from our research, and some important determinants for further modification of steroids towards the development of novel drug candidates are identified.
Synthesis and biological evaluation of 3-tetrazolo steroidal analogs: Novel class of 5α-reductase inhibitors
Aggarwal, Saurabh,Mahapatra, Manoj Kumar,Kumar, Rajnish,Bhardwaj, Tilak R.,Hartmann, Rolf W.,Haupenthal, J?rg,Kumar, Manoj
, p. 779 - 788 (2016/02/09)
In the present study, a series of steroidal tetrazole derivatives of androstane and pregnane have been prepared in which the tetrazole moiety was appended at C-3 and 17a-aza locations. 3-Tetrazolo-3,5-androstadien-17-one (6), 3-tetrazolo-19-nor-3,5-androstadien-17-one (10), 3-tetrazolo-3,5-pregnadien-20-one (14), 17a-substituted 3-tetrazolo-17a-aza-d-homo-3,5-androstadien-17-one (26-31) and 3-(2-acetyltetrazolo)-17a-aza-d-homo-3,5-androstadien-17-one (32) were synthesized from dehydroepiandrosterone acetate (1) through multiple synthetic steps. Some of the synthesized compounds were evaluated for their in vitro 5α-reductase (5AR) inhibitory activity by measuring the conversion of [3H] androstenedione in human embryonic kidney (HEK) cells. In vivo 5α-reductase inhibitory activity also showed a significant reduction (p 50 being 15.6 nM as compared to clinically used drug finasteride (40 nM). There was also a significant inhibition of 5AR-1 with IC50 547 nM compared to finasteride (453 nM).
Protein-binding properties of a designed steroidal lactam compound
Zhang, Hua-Xin,Liu
, p. 30 - 36 (2014/01/17)
Introducing amide bonds into a steroid nucleus or its side chain may reduce the acute toxicity and enhance the pharmaceutical activity. In this work, a designed steroidal amide compound, named 3β-hydroxy-17-aza-d-homo-5- androsten-17-one (HAAO), was synthesized and identified. The interactions between HAAO and human serum albumin (HSA) were studied by multiple spectroscopic methods and molecular modeling procedures. It was found that HAAO locates in Sudlow's site I in subdomain IIA of HSA molecules, relying on hydrogen bonds and van der Waals power to form HAAO-HSA complexes at ground state. The number of binding sites, binding constants, enthalpy change (ΔHθ), Gibbs free energy change (ΔG θ) and entropy change (ΔSθ) were calculated at different temperatures based on fluorescence quenching theory and classical thermodynamic equation. The percentages content of the HSA's secondary structures in presence of HAAO were detected by circular dichroism (CD) spectra and compared with those in no presence of HAAO. In addition, the experimental results of both binding site and conformational change were further confirmed by molecular modeling investigation, in which more details of the binding were visually unfolded. The information provided by the study may be useful for designing novel chemotherapeutic drugs and be helpful both in the early stages of drug discovery and in clinical practice.
Synthesis and biological evaluation of novel unsaturated carboxysteroids as human 5α-reductase inhibitors: A legitimate approach
Aggarwal, Saurabh,Thareja, Suresh,Bhardwaj,Haupenthal, Joerg,Hartmann,Kumar, Manoj
supporting information; experimental part, p. 728 - 739 (2012/09/22)
In the present study, novel steroidal 17a-substituted 3-cyano-17a-aza-D- homo-3,5-androstadien-17-ones (12-19) and 17a-substituted 17-oxo-17a-aza-D-homo- 3,5-androstadien-3-oic acids (20-26) were synthesized from dehydroepiandrosterone acetate (6) along with 17-oxo-19-nor-3,5-androstadien-3- oic acid (30) through a multistep synthesis. Compounds were evaluated for their in vitro 5α-reductase inhibitory activity by measuring the conversion of [3H] androstenedione in human embryonic kidney (HEK) cells. In vivo 5α-reductase inhibitory activity was also determined using rat prostate weighing method. Compounds 21-23 and 25 showed potent inhibition of 5α-reductase II enzyme with IC50 values of 54.1 ± 9.5, 22.1 ± 2.4, 72.8 ± 2.3 and 26.5 ± 4.4 nM respectively as compared to Finasteride (30.3 nM) along with a significant (p 0.05) reduction in rat prostate weight.
Synthesis and cytotoxicity of 17a-aza-d-homo-androster-17-one derivatives
Huang, Yanmin,Cui, Jianguo,Zhong, Zhengguo,Gan, Chunfang,Zhang, Wenyan,Song, Huacan
experimental part, p. 3641 - 3643 (2011/08/06)
A series of 17a-aza-D-homo-andrester-17-one derivatives, bearing hydroxyl, hydroximino, carbonyl and thiosemicarbazido groups at the position-3 or position-6 of steroidal nucleus, were prepared and evaluated in vitro against two human cell lines (Hela (human cervical carcinoma) and SMMC 7404 (human liver carcinoma)). The results showed that these compounds could exhibit a high cytotoxicity to Hela tumor cell line, especially for compounds 8 and 12, the IC50 values are 15.1 and 14.0 nmol/mL, respectively. Our findings could provide new evidence showing the relationship between the chemical structure and biological activity and may be useful for the discovery of new anti-cancer drugs.
Synthesis, antiproliferative, acute toxicity and assessment of antiandrogenic activities of some newly synthesized steroidal lactams
Dhingra, Neelima,Bhardwaj,Mehta, Neeraj,Mukhopadhyay, Tapas,Kumar, Ashok,Kumar, Manoj
scheme or table, p. 2229 - 2236 (2010/06/16)
The 17-oxo-17a-aza-d-homo-5-androsten-3β-yl esters (13-22) were synthesized from commercially available (25R)-5-spirosten-3β-ol (Diosgenin) (6) as starting material. The synthesized compounds were evaluated for their antiproliferative activity, acute toxicity and effect on serum androgen level and were compared with Finasteride as positive controls. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data and pharmacological screening for the synthesized compounds were reported.
Mild manganese(III) acetate catalyzed allylic oxidation: Application to simple and complex alkenes
Shing, Tony K. M.,Yeung, Ying-Yeung,Su, Pak L.
, p. 3149 - 3151 (2007/10/03)
Manganese(III) acetate catalyzed allylic oxidation of alkenes to the corresponding enones was investigated, showing excellent regioselectivity and chemoselectivity (functional group compatibility). Δ5-Steroids were transformed into bioactive Δ5-en-7-ones under a nitrogen atmosphere, whereas simple alkenes were converted into the corresponding enones under an oxygen atmosphere in good yields.
Synthetic Approaches to the Ring System of Nicandra (Benzenoid Ring D) Steroids
Blumbach, J.,Hammond, D. A.,Whiting, D. A.
, p. 261 - 268 (2007/10/02)
The androstenolone derivative (5) has been converted into the aromatic ring D steroid (39), with the C/D system of the novel natural steroid Nic-10.The route employs the seco-acid (15) which is cyclised to the D-enone (16).Selective D-aromatisation was en
