10-deacetyl taxol-C | 154677-95-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 10-deacetyl taxol-C
• 英文别名: 10-β-deacetyl-taxol C；N-hexanoyl-10-deacetyl-N-debenzoylpaclitaxel；10-Deacetyltaxayunnanine A；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 154677-95-9
• 化学式: C₄₄H₅₅NO₁₃
• 分子量: 805.92
• InChiKey: OUZGCGZMZBOCBH-MNLIZOKASA-N

物化性质

• 沸点：
  932.7±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  215
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  紫杉醇 C 在 咪唑 、 氟化氢吡啶 、 一水合肼 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 10-deacetyl taxol-C
  参考文献：
  名称：

  Single-site chemical modification at C10 of the baccatin III core of paclitaxel and Taxol C reduces P-glycoprotein interactions in bovine brain microvessel endothelial cells

  摘要：

  A single-site modification of paclitaxel analogs at the C10 position on the baccatin III core that reduces interaction with P-glycoprotein in bovine brain microvessel endothelial cells is described. Modification and derivatization of the C10 po\sition were carried out using a substrate controlled hydride addition to a key C9 and C10 diketone intermediate. The analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to paclitaxel. P-glycoprotein interaction was examined using a rhodamine assay and it was found that simple hydrolysis or epimerization of the C10 acetate of paclitaxel and Taxol C can reduce interaction with the P-glycoprotein transporter that may allow for increased permeation of taxanes into the brain. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.063

文献信息

• Process for the production of important taxol analogues 10-deacetyl
  申请人：Council of Scientific and Industrial Research

  公开号：US06028206A1

  公开（公告）日：2000-02-22

  The present invention relates to an improved process for the production of important taxol analogues 10-deacetyl taxol A,B and C of the formula (2) ##STR1## R=C.sub.6 H.sub.5 (10 deacetyl taxol A) =CH.sub.3 C.dbd.CHCH.sub.3 (10-deacetyl taxol B) =C.sub.5 H.sub.11 (10-deacetyl taxol C) where R represent C.sub.6 H.sub.5 (10-deacetyl taxol A) or, CH.sub.3 C.dbd.CHCH.sub.3 (10-deacetyl taxol B) or, C.sub.5 H.sub.11 (10-deacetyl taxol C) which comprises (a) dissolving the taxol analogues 7-xylosyl-10-deacetyl taxol A,B,C of the formula (1) ##STR2## R=C.sub.6 H.sub.5 (10 deacetyl taxol A) =CH.sub.3 C.dbd.CHCH.sub.3 (10-deacetyl taxol B) =C.sub.5 H.sub.11 (10-deacetyl taxol C) where R represents C.sub.6 H.sub.5 (taxol analogue A or xyloside A), or CH.sub.3 C.dbd.CHCH.sub.3 (taxol analogue B or xyloside B) or C.sub.5 H.sub.11 (taxol analogue C or xyloside C) in a polar solvent (b) reacting the resultant solution with periodate for 20-40 hours at 20-40.degree. C. to cleave the diol system of the xyloside into dialdehyde, (c) treating the generated dialdehyde in a mixture of polar solvent-organic acid mixture with salts of amines at 0-40.degree. C. for 12-18 hours and (d) isolating the 10-deacetyl taxol A,B,C by chromatography.

  本发明涉及一种改进的生产重要紫杉醇类似物10-去乙酰紫杉醇A、B和C的工艺，其化学式为(2)： 其中R=C.sub.6 H.sub.5 (10-去乙酰紫杉醇A) =CH.sub.3 C.dbd.CHCH.sub.3 (10-去乙酰紫杉醇B) =C.sub.5 H.sub.11 (10-去乙酰紫杉醇C)；其中R代表C.sub.6 H.sub.5 (10-去乙酰紫杉醇A)或，CH.sub.3 C.dbd.CHCH.sub.3 (10-去乙酰紫杉醇B)或，C.sub.5 H.sub.11 (10-去乙酰紫杉醇C)。该工艺包括以下步骤：(a)将紫杉醇类似物7-木糖基-10-去乙酰紫杉醇A、B、C的化学式(1)： 其中R=C.sub.6 H.sub.5 (10-去乙酰紫杉醇A或木糖苷A)，或CH.sub.3 C.dbd.CHCH.sub.3 (10-去乙酰紫杉醇B或木糖苷B)，或C.sub.5 H.sub.11 (10-去乙酰紫杉醇C或木糖苷C)在极性溶剂中溶解；(b)将产生的溶液与高碘酸在20-40℃反应20-40小时，以将木糖苷的二醇系统裂解成二醛；(c)将生成的二醛在极性溶剂-有机酸混合物中与胺盐在0-40℃反应12-18小时；(d)通过色谱法分离10-去乙酰紫杉醇A、B、C。
• Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol
  作者：Kang Wang、Tingting Wang、Jianhua Li、Jianhua Zou、Yongqin Chen、Jungui Dai

  DOI：10.1016/j.molcatb.2010.11.013

  日期：2011.3

  Enterobacter sp. CGMCC 2487, a bacterial strain isolated from the soil around a Taxus cuspidata Sieb. et Zucc. plant, was able to remove the xylosyl group from 7-xylosyltaxanes. The xylosidase of this strain was an inducible enzyme. In the bioconversion of 7-xylosyl-10-deacetyltaxol (7-XDT) to 10-deacetyltaxol (10-DT), for the purpose of enhancing the conversion efficiency, the effects of NH4+, oat xylan, temperature, pH value, cell density and substrate concentration on the bioconversion have been systematically investigated. 3.0 mM NH4+, 0.6% oat xylan in the media could enhance the yield of 10-DT; the optimum biocatalytic temperature was 26 degrees C and optimum pH value was 6.0. The highest conversion rate and yield of 10-DT from 7-XDT reached 92% and 764 mg/L, respectively. In addition, the biocatalytic capacity of the cell cultures remained 66.1% after continuous three batches. These results indicate that converting 7-XDT to 10-DT, a useful intermediate for the semisynthesis of paclitaxel or other taxane-based anticancer drugs by a novel bacterial strain, Enterobacter sp. CGMCC 2487, would be an alternative for the practical application in the future. (C) 2010 Elsevier B.V. All rights reserved.