3α,7α,12α-triacetoxy-5β-cholan-24-ol | 20171-56-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3α,7α,12α-triacetoxy-5β-cholan-24-ol
• 英文别名: 3α,7α,12α-triacetoxy-5β-cholane-24-ol；3α,7α,12α-O-triacetyl-24-hydroxycholane；3alpha,7alpha,12alpha-Triacetoxy-24-hydroxy-5beta-cholane；[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diacetyloxy-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 20171-56-6
• 化学式: C₃₀H₄₈O₇
• 分子量: 520.707
• InChiKey: ZAYWNOWWQFFEQH-GATWWBNQSA-N

物化性质

• 沸点：
  572.4±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3α,7α,12α-triacetoxy-5β-cholan-24-ol 在 三乙酰氧基硼氢化钠 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 N-methyl-N-(3α,7α,12α-triacetoxy-5β-cholan-24-yl)-N′-(7′-chloroquinolin-4′-yl)ethane-1,2-diamine
  参考文献：
  名称：

  Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease andP. falciparumMalaria

  摘要：

  Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.

  DOI：

  10.1021/jm500033r
• 作为产物：
  描述：

  胆酸 在 4-二甲氨基吡啶 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 5.0h， 生成 3α,7α,12α-triacetoxy-5β-cholan-24-ol
  参考文献：
  名称：

  有效合成7alpha，12alpha-dihydroxy-4-cholesten-3-one及其生物前体7alpha-hydroxy-4-cholesten-3-one：胆汁酸生物合成中的关键中间体。

  摘要：

  本文介绍了化学合成7alpha，12alpha-dihydroxy-4-cholesten-3-one（1a）及其生物学前体7alpha-hydroxy-4-cholesten-3-one（1b）的方法。胆固醇从胆汁酸生物合成的主要途径中的关键中间体。涉及的主要反应是（1）通过胆甾醇（异戊烷）的3碳延伸形成胆固醇（异辛烷）侧链，（2）氧化序列以转化甾体A的3α-羟基/ B环形成所需的4-en-3-one系统，以及（3）对甾体原子核中C-7和C-12位置的羟基的适当保护策略。1a和1b的绝对结构通过NMR和X射线晶体学确认。从2a和2b分别分11步制备的目标化合物1a和1b，

  DOI：

  10.1016/j.steroids.2013.05.011

文献信息

• Novel 4-Aminoquinolines Active against Chloroquine-Resistant and Sensitive <i>P. falciparum</i> Strains that also Inhibit Botulinum Serotype A
  作者：Bogdan A. Šolaja、Dejan Opsenica、Kirsten S. Smith、Wilbur K. Milhous、Nataša Terzić、Igor Opsenica、James C. Burnett、Jon Nuss、Rick Gussio、Sina Bavari

  DOI：10.1021/jm800737y

  日期：2008.8.1

  excellent in vitro antimalarial activities (IC90 (W2) down to 6.74 nM). The same entities also inhibit the botulinum neurotoxin serotype A light chain metalloprotease at low micromolar levels (7-31 microM). Interestingly, structural features imparting increased antimalarial activity also provide increased metalloprotease inhibition, thus allowing for simultaneous compound optimizations against distinct targets

  我们报告了将4-氨基-7-氯喹啉与甾体和金刚烷成分偶联以提供具有出色的体外抗疟活性（IC90（W2）低至6.74 nM）的小分子的初步结果。相同的实体还以低微摩尔水平（7-31 microM）抑制肉毒杆菌神经毒素血清型A轻链金属蛋白酶。有趣的是，赋予增加的抗疟活性的结构特征也提供了增加的金属蛋白酶抑制，因此允许针对不同靶同时进行化合物优化。
• New 9-aminoacridine derivatives as inhibitors of Botulinum neurotoxins and P. falciparum malaria
  作者：Miklos Tot、Dejan Opsenica、Milena Mitric、James Burnett、Laura Gomba、Sina Bavari、Bogdan Solaja

  DOI：10.2298/jsc130924112t

  日期：——

  Steroidal and adamantane aminoacridine derivatives were prepared and tested as both botulinum neurotoxin (BoNT) inhibitors and antimalarials. Steroid-bound acridines provided good potency against both the BoNT/A and BoNT/B light chains (LCs). The observed inhibition of the BoNT/B LC by ca. 50% is the highest attained inhibitory activity against this serotype by acridine-based compounds to date. With respect to antimalarial activity, adamantane acridines were the most potent derivatives (IC50 = 6-9 nM, SI > 326), indicating that an adamantyl group is a better carries than a steroidal motif for this indication.

  制备了类固醇和金刚烷氨基吖啶衍生物，并将其作为肉毒杆菌神经毒素（BoNT）抑制剂和抗疟药物进行了测试。 作为肉毒杆菌神经毒素（BoNT）抑制剂和抗疟药物进行了测试。 类固醇结合的吖啶对 BoNT/A 和 BoNT/B轻链（LCs）都有很好的抑制作用。所观察到的对 BoNT/B LC 的抑制率约为 50%，是所达到的最高抑制率。 50%，这是迄今为止吖啶类化合物对该血清型达到的最高抑制活性。 吖啶类化合物对该血清型的最高抑制活性。在抗疟活性方面 金刚烷吖啶是最有效的衍生物（IC50 = 6-9 nM，SI >； 326），这表明金刚烷基比甾族 基团。
• Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative
  作者：Rika Satoh、Hiroaki Ogata、Tetsuya Saito、Biao Zhou、Kaoru Omura、Satoshi Kurabuchi、Kuniko Mitamura、Shigeo Ikegawa、Lee R. Hagey、Alan F. Hofmann、Takashi Iida

  DOI：10.1007/s11745-016-4150-0

  日期：2016.6

  Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes Buceros bicornis (great hornbill) and Penelopides panini (Visayan tarictic hornbill). Their structures were determined to be 3alpha,7alpha,24-dihydroxy-5beta-cholestan-27-oic acid and its 12alpha-hydroxy derivative, 3alpha,7alpha,12alpha,24-tetrahydroxy

  从鸟类犀牛科的Bucerotidae科的两种犀鸟的胆囊胆汁中分离出两种主要胆汁酸。确定其结构为3α，7α，24-二羟基-5β-胆甾醇-27-oic酸及其12α-羟基衍生物，3α，7α，12α，24-四羟基-5β-胆甾醇-27-oic酸（戊酸，VA），两者均以胆汁中的牛磺酸酰胺化物形式存在于胆汁中。合成了四种钒酸的非对映异构体，并通过X射线晶体学分析确定了它们的指定结构。发现VA及其12-脱氧衍生物具有（24R，25S）构型。还通过HPLC分析了另外13种犀鸟物种，它们显示出与双歧双歧杆菌和帕尼尼假单胞菌相似的胆汁酸模式。
• New Silybin Scaffold for Chemical Diversification: Synthesis of Novel 23-Phosphodiester Silybin Conjugates
  作者：Giovanni Di Fabio、Armando Zarrelli、Valeria Romanucci、Marina Greca、Lorenzo De Napoli、Lucio Previtera

  DOI：10.1055/s-0032-1317688

  日期：——

  Silybin is the major component (ca. 30%) of the silymarin complex extracted from the seeds of Silybum marianum, with multiple biological activities operating at various cell levels. As an ongoing effort toward the exploitation of natural products as scaffolds for chemical diversification at readily accessible positions, we present here an efficient synthetic procedure to obtain new 23-phosphodiester silybin conjugates with different labels. A key point in our approach is the new 3,5,7,20-tetra-O-acetylsilybin-23-phosphoramidite, useful for a variety of derivatizations following a reliable and well-known chemistry. The feasibility of the procedure has been demonstrated by preparing new 23-silybin conjugates, exploiting standard phosphoramidite chemistry.
• Kuramoto, Taiju; Kihira, Kenji; Matsumoto, Naoko, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 4, p. 1136 - 1139
  作者：Kuramoto, Taiju、Kihira, Kenji、Matsumoto, Naoko、Hoshita, Takahiko

  DOI：——

  日期：——