35961-41-2Relevant articles and documents
High-field NMR studies of 3β-tetrahydropyranyloxy steroids
Szendi, Zsuzsanna,Forgo, Peter,Koever, Katalin E.,Sweet, Frederick
, p. 415 - 422 (2000)
Comprehensive NMR studies were carried out on 3β-hydroxy-pregnene and cholestene analogs, each containing a tetrahydropyranyl ether group at the 3-position. Two-dimensional NMR experiments (COSY, TOCSY, HSQC, and HSQC-TOCSY) permitted the complete assignments of both the 1H and 13C resonances of these derivatives in deuterated benzene or chloroform. The aromatic solvent-induced NMR signal shifts (ASIS) were also investigated. Copyright (C) 2000 Elsevier Science Inc.
Synthesis and Evaluation of Osteogenic Oxysterols as Hedgehog Pathway Activators
Maschinot, Chad A.,Corman, Audrey R.,Deberardinis, Albert M.,Hadden, M. Kyle
, p. 679 - 686 (2016)
Oxysterols (OHCs) are metabolic byproducts of cholesterol that are known to function as agonists of the Hedgehog (Hh) signaling pathway. Previously, we reported 23(S)-hydroxycholesterol [23(S)-OHC, 4] as a potent activator of Hh signaling with the ability to functionally differentiate mouse embryonic fibroblasts to an osteogenic fate. To obtain 23(S)-OHC in quantities suitable for invivo evaluation, we developed a revised synthetic route that decreases the number of steps and chromatographic purifications, and which also enhances the stereoselective nature of the synthesis. This new route also allows access to the C21 methyl group of the OHC scaffold, and several new analogues with varying stereochemistry at this location were evaluated for their ability to up-regulate the Hh pathway.
Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays
Katoch, Rita,Korde, Shilpa S.,Deodhar,Trivedi, Girish K.
, p. 1741 - 1754 (1999)
The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3β-ol-20S-yl)methyl]oate]-2',2',5',5'- tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3-one-20S-yl)methyl]oate]- 2',2',5',5'-tetra methyl pyrrolidine-1'-oxyl, 3'-[(3β-acetoxypregn-5-en-20- one-16α-yl)prop-2'ξ-ol-3'ξ-oate]-2',2',5',5'-tetramethyl pyrrolidine-1- oxyl and 3-[(pregn-5-en-3,20-dione-16α-yl)prop-2'ξ-ol-3'ξ-oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons.
Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia.
Zheng, Gang,Li, Hui,Yang, Kathy,Blessington, Dana,Licha, Kai,Lund-Katz, Sissel,Chance, Britton,Glickson, Jerry D
, p. 1485 - 1488 (2002)
For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner.
New crystalline form of vascular leak blocker compound
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Paragraph 0161; 0189; 0192-0195, (2021/03/16)
The present invention relates to a crystalline form of (E)-methyl 6-((3S,8S,9S,10R,13S,14S,17R)-3-(((5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-yl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)hept-5-enoate and a vascular leakage blocker comprising same. The novel crystalline form has high purity and excellent stability with consequent excellent long-term storage and pharmaceutical stability, and is available for use as a vascular leakage blocker, and as such, is very advantageous in producing high-quality drug substances.
Preparation method of vascular leakage blockers with a high yield
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Paragraph 0167-0175, (2020/08/01)
The present invention relates to a high-yield preparation method of a novel vascular leakage blocker. The preparation method facilitates a reaction process, has higher productivity and economy compared to conventional methods by being used as an intermediate facilitating removal of impurities generated during the reaction, has high yield by using a new reagent not previously used in a step of generating an isomer to prepare the novel vascular leakage blocker, and is very advantageous for preparing high quality raw material medicine.COPYRIGHT KIPO 2020
20-triazole-20-hydroxyl-pregnane derivatives, method for preparing same and medical application of 20-triazole-20-hydroxyl-pregnane derivatives
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Paragraph 0089; 0090; 0091, (2018/11/22)
The invention belongs to the field of medicines, and particularly relates to a series of 20-triazole-20-hydroxyl-pregnane derivatives, a method for preparing the same and medical application of the 20-triazole-20-hydroxyl-pregnane derivatives. The 20-triazole-20-hydroxyl-pregnane derivatives are particularly used for preparing medicines for treating androgen receptor related diseases such as cellproliferation, prostate cancer, polytrichia, acne and androgenic alopecia which are dependent on androgens. Structural general formulas of compounds of the 20-triazole-20-hydroxyl-pregnane derivativesare shown. Details of definition of various groups in the general formulas are attached to specifications.
Glucal-conjugated sterols as novel vascular leakage blocker: Structure-activity relationship focusing on the C17-side chain
Kim, Kyeojin,Maharjan, Sony,Lim, Changjin,Kim, Nam-Jung,Agrawal, Vijayendra,Han, Young Taek,Lee, Sujin,An, Hongchan,Yun, Hwayoung,Choi, Hyun-Jung,Kwon, Young-Guen,Suh, Young-Ger
, p. 184 - 194 (2014/03/21)
A series of glucal-conjugated sterols as novel vascular leakage blocker were identified through design, synthesis and biologically evaluation. In addition, the structure-activity relationship (SAR) of the glucal-conjugated sterols focusing on the C17-side chain was also established. The sterol analogs linked with the rigid C17-side chain side chains exhibited potent cell survival activities. In particular, analog 21l, which possesses a cyclopentyl oxime moiety, was shown to have excellent pharmacological effects on retinal vascular leakage in a diabetic mouse model.
NOVEL VASCULAR LEAK INHIBITOR
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Page/Page column 39-40, (2012/09/21)
The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present disclosure inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, enhances the cortical actin ring structure, and improves the stability of the tight junctions (TJs) between vascular cells, thereby inhibiting vascular leakage. The vascular leakage inhibitor of the present disclosure has the activity of not only reducing vascular permeability but also recovering the integrity of damaged blood vessels. Accordingly, the vascular leakage inhibitor of the present disclosure can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present disclosure is synthesized from commercially available or easily synthesizable cholesterols, it has remarkably superior feasibility of commercial synthesis.
SYNTHESIS OF PERFLUOROALKYL STEROIDS AS CO-EMULSIFYING AGENTS FOR 1-BROMOPERFLUOROOCTANE AND OTHER PERFLUOROCOMPOUNDS
Sharts, C. M.,Malik, A. A.,Easdon, J. C.,Khawli, L. A.,Long, D. M.,et. al.
, p. 365 - 384 (2007/10/02)
Syntheses of steroids substituted with perfluoroalkyl groups at C-3, C-7, and C-20 positions on the steroid nucleus are described.Synthetic methods employed included coupling of perfluoroalkylcopper with allylic bromides and Grignard reactions.Free radical additions of perfluoroalkyl iodide to unsaturated steroids and reaction of perfluoroalkyl Grignard reagents with 6-ketosteroid were unsuccessful.Perfluoroalkyl-substituted steroids are desired for testing as co-emulsifying agents in perfluorooctyl bromide/water emulsions which are used as blood substitutes (synthetic blood).A rationale for the choice of perfluorooctyl bromide as the oxygen-carrying agent in the fluorocarbon-based blood substitute and on the use of perfluoroalkyl-substituted steroids as co-emulsifying agents is also reported.
