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24150-24-1

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24150-24-1 Usage

Uses

Terameprocol is a synthetic derivative of NDGA and non-selective lipoxygenase inhibitor.

Biological Activity

tetramethyl nordihydroguaiaretic acid (tmndga) is a synthetic derivative of ndga (nordihydroguaiaretic acid), a non-selective lipoxygenase inhibitor. tmndga showed the strongest anti-hiv activity.

in vitro

in vero cells, tmndga inhibited sp1 transcription factor binding at the hiv long terminal repeat promoter and at the α-icp4 promoter with ic50 values of 11 and 43.5 μm, respectively. the ic50 of tmndga varied between 11.7 and 4 μm in 10 passages of hsv-1 and 4 passages of hsv-2 [2]. tmndga inhibited sp1-dependent cdc2 gene expression. in m4n-treated transformed c3 cells, tmndga induced growth arrest and apoptosis by suppressing sp1-dependent cdc2 and survivin gene expression giving rise to its antitumorigenic activity [3]. tmndga treatment suppressed expression of the sp1-dependent survivin gene. in transiently and stably survivin-transfected c3 cells, tmndga reduced caspase-3 activation by 50% and 75%, respectively [3]. tmndga inhibited the growth of a number of tumor cell lines by inducing apoptosis in a non-schedule-dependent manner [4]. tmndga inhibited the synthesis of dna by melanoma cells and causes cell cycle arrest in g0/g1 and g2/m phases of the cell cycle [4].

in vivo

tmndga effectively inhibited the growth of human tumors in nude mice [5]. tmndga inhibited the growth of both murine and human melanomas and human colon cancer without apparent hepatic or renal toxicity [4]. in nude (nu/nu) mice bearing xenografts of human tumor types (hep 3b, lncap, ht-29, mcf7, and k-562), treatment with tmndga (i.v. or i.p.) down-regulated cdc2 and survivin genes expression [5].

references

[1] hwu j r, tseng w n, gnabre j, et al. antiviral activities of methylated nordihydroguaiaretic acids. 1. synthesis, structure identification, and inhibition of tat-regulated hiv transactivation[j]. journal of medicinal chemistry, 1998, 41(16): 2994-3000.[2] chen h, teng l, li j n, et al. antiviral activities of methylated nordihydroguaiaretic acids. 2. targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor tetra-o-methyl-ndga[j]. journal of medicinal chemistry, 1998, 41(16): 3001-3007.[3] chang c c, heller j d, kuo j, et al. tetra-o-methyl nordihydroguaiaretic acid induces growth arrest and cellular apoptosis by inhibiting cdc2 and survivin expression[j]. proceedings of the national academy of sciences of the united states of america, 2004, 101(36): 13239-13244.[4] lambert j d, meyers r o, timmermann b n, et al. tetra-o-methylnordihydroguaiaretic acid inhibits melanoma in vivo[j]. cancer letters, 2001, 171(1): 47-56.[5] park r, chang c c, liang y c, et al. systemic treatment with tetra-o-methyl nordihydroguaiaretic acid suppresses the growth of human xenograft tumors[j]. clinical cancer research, 2005, 11(12): 4601-4609.

Check Digit Verification of cas no

The CAS Registry Mumber 24150-24-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,1,5 and 0 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 24150-24:
(7*2)+(6*4)+(5*1)+(4*5)+(3*0)+(2*2)+(1*4)=71
71 % 10 = 1
So 24150-24-1 is a valid CAS Registry Number.

24150-24-1 Well-known Company Product Price

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  • Sigma

  • (T3455)  Terameprocol  ≥98% (HPLC)

  • 24150-24-1

  • T3455-10MG

  • 713.70CNY

  • Detail
  • Sigma

  • (T3455)  Terameprocol  ≥98% (HPLC)

  • 24150-24-1

  • T3455-50MG

  • 2,932.02CNY

  • Detail

24150-24-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name meso-tetra-O-methyl nordihydroguaiaretic acid

1.2 Other means of identification

Product number -
Other names tetramethyl Nordihydroguaiaretic Acid Exclusive

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:24150-24-1 SDS

24150-24-1Relevant articles and documents

Inhibitors of adenosine 3',5'-cyclic monophosphate phosphodiesterase from Schisandra chinensis and the structure activity relationship of lignans

Sakurai,Nikaido,Ohmoto,Ikeya,Mitsuhashi

, p. 1191 - 1195 (1992)

The structure activity relationship was studied in analogous lignans from Schisandra chinensis and their derivatives. These compounds were tested for cyclic adenosine 3',5'-monophosphate (cAMP) phosphodiesterase inhibition. An inhibitor, nordihydroguaiaretic acid (13), was isolated from this plant, so we discussed this compound and a derivative, nordihydroguaiaretic acid tetramethyl ether, using molecular mechanics involving three-dimensional modeling and minimization of the structure using the MM2PP program. As a result, it was found that the structure of nordihydroguaiaretic acid tetramethyl ether and papaverine (30) (positive control) shared a similar low energy conformation. This fact suggested that these compounds inhihited cAMP phosphodiesterase by a similar mechanism.

A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

Alfonzo, Edwin,Beeler, Aaron B.

, p. 7746 - 7754 (2019/08/30)

Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.

Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines

Li, Xu,Jiang, Jian-Hong,Chen, Qingqi,Xiao, Sheng-Xiong,Li, Chuan-Hua,Gu, Hui-Wen,Zhang, Hui,Hu, Ji-Lin,Yao, Fei-Hong,Li, Qiang-Guo

, p. 605 - 613 (2013/06/05)

Nordihydroguaiaretic acid (NDGA) and its synthetic analogues are potentially useful in treating diseases related to cancers, diabetes, viral and bacterial infections, and inflammation. In this paper, we report the optimal synthetic methods and the bioactivity study of terameprocol 2, NDGA derivative 3, and its cyclized analogue 4. The IC50 of these three compounds 2, 3 and 4 on the growth metabolism of Schizosacchromyces pombe and K562 cell lines were determined by microcalorimetry. The preliminary results showed that the compounds 2, 3 and 4 possessed good inhibition activities on S. pombe and K562 cell lines, and exhibited bidirectional biological effect and Hormesis effect. In particular, terameprocol 2 was found to possess the most potent inhibitory effect on K562 cell lines.

SCALABLE SYNTHETIC PROCESS FOR MAKING TERAMEPROCOL

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Page/Page column 33-34, (2010/04/03)

A manufacturing process for making terameprocol (1) which includes the following reaction scheme, wherein a first general reaction is the formation of a furan intermediate (39) and a second general reaction is the ring-reduction and ring-opening of the furan intermediate (39) to form the terameprocol (1)

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