Synthesis and biological activities of 8(14)a-homocalcitriol

Steinmeyer, Andreas; Neef, Günter; Kirsch, G.; Schwarz, Katica; Rach, P.; Haberey, Martin; Thieroff-Ekerdt, Ruth

doi:10.1016/0039-128x(92)90099-u

Cited by 14 publications

(14 citation statements)

References 18 publications

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“…Since the antiproliferative activities of calcitriol are believed to be of genomic nature, the initial test for assessing vitamin D activity in vitro was the VDR binding either anti-psoriatic activity and anti-tumor effects in vitro. Since the major goal of every drug finding program in the vitamin D field is the reduction of hypercalcemic activity of the new analogs compared to calcitriol, the calcitropic effects of the newly synthesized derivatives were examined in vivo due to the lack of a predictive in vitro surrogate for hypercalcemia [10]. Hence, intact rats were treated subcutaneously with calcitriol analogs.…”

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

“…For evaluation of the biological activities of the Schering calcitriol analogs, a routine screening process was established [10]. Since the antiproliferative activities of calcitriol are believed to be of genomic nature, the initial test for assessing vitamin D activity in vitro was the VDR binding either anti-psoriatic activity and anti-tumor effects in vitro.…”

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

“…Now the usual sequence could be pursued to introduce the 23-oxa side chains which finally led to the analogs 82 (R=Me), 83 (R=Et), and 84 (R=Pr). These iso-19-nor calcitriol analogs were biologically tested by applying the test protocols which have been discussed before (Table 3) [10].…”

Section: -Nor-23-oxa Calcitriolsmentioning

confidence: 99%

“…As a prominent assay reflecting vitamin D activity on cancer cells in vitro, the induction of differentiation of the human promyelocytic cell line HL 60 to monocytes and macrophages was applied [10,13]. Additionally, to investigate the effects of the Schering analogs on skin cells, a murine keratinocyte preparation was used initially [10,14]. Already in the beginning of the drug finding program it became clear that the inhibitory effects of calcitriol derivatives on the proliferation of keratinocytes completely correlate with the ability to induce HL 60 differentiation.…”

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

“…Nevertheless, in the course of the vitamin D program at Schering binding affinities for human DBP were examined in comparison with calcitriol and 25-hydroxyvitamin D 3 , the best DBP binder known. As a prominent assay reflecting vitamin D activity on cancer cells in vitro, the induction of differentiation of the human promyelocytic cell line HL 60 to monocytes and macrophages was applied [10,13]. Additionally, to investigate the effects of the Schering analogs on skin cells, a murine keratinocyte preparation was used initially [10,14].…”

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

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New Synthetic Vitamin D Analogs with Antiproliferative Activities

Steinmeyer¹,

Kirsch²,

Neef³

et al. 2000

CPD

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The introduction of oxygen atoms into different positions of the vitamin D side chain is described. By combining the arising 23-oxa and 25-oxa elements with other structural modifications (19-nor, iso-19-nor, 20-methyl, 20-ene, 20,21-cyclo) calcitriol analogs with remarkable levels of dissociation between beneficial acitivities on cell growth regulation and undesired hypercalcemia were identified. Structure-activity relations are elaborated in a very systematic outline of the Schering drug finding program in this particular class of vitamin D compounds.

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Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

Section: -Nor-23-oxa Calcitriolsmentioning

confidence: 99%

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

Section: -Oxa Calcitriols -Parent Seriesmentioning

confidence: 99%

See 3 more Smart Citations

New Synthetic Vitamin D Analogs with Antiproliferative Activities

Steinmeyer¹,

Kirsch²,

Neef³

et al. 2000

CPD

Self Cite

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Simmons‐Smith Cyclopropanation Reaction

2001

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Almost 30 years after Emschwiller prepared IZnCH 2 I, Simmons and Smith discovered that the reagent formed by mixing a zinc‐copper couple with CH 2 I 2 in ether could be used for the stereospecific conversion of alkenes to cyclopropanes. Nowadays, the Simmons‐Smith cyclopropanation reaction is one of the most widely used reactions in the organic chemist's arsenal for the conversion of olefins into cyclopropanes. This popularity is mainly due to the stereospecificity of the reaction with respect to the double bond geometry and its compatibility with a wide range of functional groups. The chemoselectivity of the reaction toward some olefins is excellent and very few side reactions are observed with functionalized substrates. The metal carbenoid is electrophilic in nature and electron‐rich alkenes usually react much faster than electron‐poor alkenes. Furthermore, the ability to use proximal hydroxy or ether groups to dictate the stereochemical outcome of the CC bond forming process was recognized early on, and this unique property has been successfully exploited on numerous occasions. It has been recognized that halomethylmetal reagents are powerful synthetic tools for the stereoselective addition of a methylene unit to chiral acyclic allylic alcohols and allylic ethers. In addition, the use of halomethylzinc reagents in the presence of chiral additives is one of the few ways to cyclopropanate allylic alcohols efficiently and with good enantiocontrol. Carbenoids can be divided into the following two classes: (1) those of general structure MCH 2 X and (2) those corresponding to M = CH 2 . This chapter is focussed exclusively on the first class in which M = Zn, Sm, or Al. Although other metal carbenoids of type MCH 2 X, such as those derived from Cu, Cd, Hg, and In, have been reported to be effective reagents for the cyclopropanation of some olefins, they have been used only sporadically, and this review does not highlight these reactions. This chapter covers cyclopropanation reactions involving haloalkylzinc, aluminum, and samarium reagents published since the comprehensive chapter in Organic Reactions by Simmons that surveyed the literature up to 1973.

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Determination of Sudan IV in hot chilli powder with luminol/dissolved oxygen chemiluminescence system

2009

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The proposed method was successfully applied to the determination of Sudan IV in contaminated hot chilli powder, with recoveries ranging from 89.3 to 108.4%. The possible mechanism of enhancement of the luminol/dissolved oxygen CL reaction by Sudan IV can be attributed to the acceleration of electron transfer. Compared with other procedures, the proposed CL method offers the highest sensitivity and the least reagent consumption for the determination of Sudan IV.

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Synthesis and biological activities of 8(14)a-homocalcitriol

Cited by 14 publications

References 18 publications

New Synthetic Vitamin D Analogs with Antiproliferative Activities

New Synthetic Vitamin D Analogs with Antiproliferative Activities

Simmons‐Smith Cyclopropanation Reaction

Determination of Sudan IV in hot chilli powder with luminol/dissolved oxygen chemiluminescence system

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