diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside | 528841-18-1

• 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: diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-5-amino-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxane-3,4-diol
• CAS: 528841-18-1
• 化学式: C₃₃H₅₃NO₇
• 分子量: 575.786
• InChiKey: RWLJYCYCDKMCBA-FQAINDKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 以28 mg的产率得到diosgenyl 2-deoxy-2-amino-β-D-glucospyranoside hydrochloride
  参考文献：
  名称：

  甾体糖缀合物的合成及选择性抗癌活性

  摘要：

  的葡糖胺衍生物的合成的甾体皂苷元薯蓣皂苷元和使用核柯配基Ñ -phthaloyl保护的三氯乙酰d葡糖胺作为供体和将TMSOTf作为启动子的报道。将相应的糖缀合物转化为其乙酰氨基衍生物和盐酸盐（来自薯os皂素），并针对HeLa，CaSki和ViBo宫颈外膜癌细胞进行测试。这些化合物对肿瘤细胞和人淋巴细胞显示出低细胞毒性值，表明主要的细胞死亡过程可能不是坏死。重要的是，这些化合物对肿瘤细胞的抗增殖活性并不影响外周血淋巴细胞的增殖潜能。

  DOI：

  10.1016/j.ejmech.2012.06.027
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 吡啶 、 甲醇 、 1,1-二氯甲醚 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 三乙胺 、 zinc(II) chloride 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 43.34h， 生成 diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside

  摘要：

  Four differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin. The following amine group protections were tested: trifluoroacetyl (TFA), 2,2,2-trichloroethoxycarbonyl (Troc), phthaloyl (Phth), and tetrachlorophthaloyl (TCP). Products of glycosylation were deprotected to yield diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside. The efficiency of the procedures is discussed. Additionally, a single-crystal X-ray diffraction analysis for 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranosyl chloride is reported. Orientations of the pyranose substituents as well as the planarity of the acetoxy and phthalimide groups in the crystal lattice are discussed. Structural evidence is presented for a mesomeric effect in both groups. The preference of the cis over trans orientation of the acetoxy group is confirmed in the crystal lattice. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.020

文献信息

• <i>N</i>-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity
  作者：Agata Walczewska、Daria Grzywacz、Dorota Bednarczyk、Małgorzata Dawgul、Andrzej Nowacki、Wojciech Kamysz、Beata Liberek、Henryk Myszka

  DOI：10.3762/bjoc.11.97

  日期：——

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi.

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside是一种具有吸引人的药理特性的合成皂苷。我们测试了不同的途径来获得这种糖苷，这里总结了这些途径。此外，还介绍了合成葡萄糖吡喃糖苷的N-烷基和N,N-二烷基衍生物。对这些衍生物的抗菌和抗真菌活性评估表明，它们对革兰氏阴性菌没有抑制活性，而许多经过测试的N-烷基皂苷被发现抑制了革兰氏阳性菌和人类病原真菌的生长。
• Activity of Diosgenyl 2-amino-2-deoxy-.-D-glucopyranoside, its Hydrochloride, and N,N-dialkyl Derivatives Against Non-albicans Candida Isolates
  作者：Malgorzata Anna Dawgul、Daria Grzywacz、Beata Liberek、Wojciech Kamysz、Henryk Myszka

  DOI：10.2174/1573406414666180226164747

  日期：2018.7.6

  OBJECTIVE In view of the emergence of non-albicans Candida and their resistance to available antifungals, an attempt has been made to develop novel effective agents. Biological activities of the N,N-dialkyl diosgenyl glycosides, which were previously synthesized, were determined. METHOD Minimum inhibitory concentration (MIC) was determined for group of clinical nonalbicans Candida isolates by serial

  背景技术白色念珠菌属于人类中最常见的真菌病原体，但是最近已经报道了称为非白色念珠菌的菌株的增殖增加。属于这一类的物种通常以对抗真菌剂的敏感性降低为特征。目的鉴于非白色念珠菌的出现及其对可用抗真菌剂的耐药性，已尝试开发新型有效药剂。测定了先前合成的N，N-二烷基二硫基糖苷的生物活性。方法采用连续稀释法，在Sabouraud液体培养基中测定临床非白色念珠菌分离株组的最低抑菌浓度（MIC）。为了评估对人细胞的毒性，在磷酸缓冲液中通过系列稀释法确定了人红细胞上的最小溶血浓度（MHC）。结果皂甙对临床分离的光滑毛状线虫和副纤毛状线虫表现出很强的活性，与常规抗微生物剂相比甚至更高。在光滑念珠菌分离物中显示出对氟康唑的高耐药率。在克鲁氏梭菌和热带梭菌的临床菌株中，鉴定出对皂苷敏感性降低的分离株。所有测试的克鲁斯克鲁维酵母分离株均显示出对氟康唑的抗性，而在热带假丝酵母中，许多菌株对所有测试的唑类均具有抗性
• Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside hydrochloride and its derivatives
  作者：Henryk Myszka、Dorota Bednarczyk、Maria Najder、Wiesław Kaca

  DOI：10.1016/s0008-6215(02)00407-x

  日期：2003.1

  2-Acetamido-2-deoxy-D-glucose hydrochloride (D-glucosamine hydrochloride) has been used for the preparation of 1,3.4.6-tetra- O-acetyl-2-deoxy-2-trifluoroacetqamido-beta- (4) and 2-tetrachlorophthalimido-alpha, beta-D-glucopyranose (6) which have been transformed into the appropriate bromides and the chloride. Both bromo and chloro sugars were used as a glycosyl donors for the glycosylation of diosgenin [(25R)-spirost-5-en-3beta-ol]. These condensations were conducted under mild conditions, using silver triflate as a promoter, and gave diosgenyl glycosides 9 and 12. Each of them was converted into diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside hydrochloride (11) and N-acylamido derivatives. The structures of all new glycosides were established by H-1 and C-13 NMR spectroscopy. These diosgenyl glycosides are the first saponins containing the D-glucosamine residue that have been synthesized. These compounds show promising antitumor activities, The synthetic saponins increase the number of apoptotic B cells, in combination with cladribine (2-CdA). that are isolated from chronic lymphotic leukemia (B-CLL) patients. (C) 2002 Published by Elsevier Science Lid.
• Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside
  作者：Dorota Bednarczyk、Agata Walczewska、Daria Grzywacz、Artur Sikorski、Beata Liberek、Henryk Myszka

  DOI：10.1016/j.carres.2012.11.020

  日期：2013.2

  Four differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin. The following amine group protections were tested: trifluoroacetyl (TFA), 2,2,2-trichloroethoxycarbonyl (Troc), phthaloyl (Phth), and tetrachlorophthaloyl (TCP). Products of glycosylation were deprotected to yield diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside. The efficiency of the procedures is discussed. Additionally, a single-crystal X-ray diffraction analysis for 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranosyl chloride is reported. Orientations of the pyranose substituents as well as the planarity of the acetoxy and phthalimide groups in the crystal lattice are discussed. Structural evidence is presented for a mesomeric effect in both groups. The preference of the cis over trans orientation of the acetoxy group is confirmed in the crystal lattice. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and selective anticancer activity of steroidal glycoconjugates
  作者：María A. Fernández-Herrera、Hugo López-Muñoz、José M.V. Hernández-Vázquez、Luis Sánchez-Sánchez、María L. Escobar-Sánchez、B. Mario Pinto、Jesús Sandoval-Ramírez

  DOI：10.1016/j.ejmech.2012.06.027

  日期：2012.8

  The synthesis of glucosamine derivatives of the steroidal sapogenins diosgenin and hecogenin using the N-phthaloyl protected trichloroacetimidate of d-glucosamine as donor and TMSOTf as promoter is reported. The corresponding glycoconjugates were transformed into their acetamido derivatives and the hydrochloride salt (from diosgenin) and tested against HeLa, CaSki, and ViBo cervicouterine cancer cells

  的葡糖胺衍生物的合成的甾体皂苷元薯蓣皂苷元和使用核柯配基Ñ -phthaloyl保护的三氯乙酰d葡糖胺作为供体和将TMSOTf作为启动子的报道。将相应的糖缀合物转化为其乙酰氨基衍生物和盐酸盐（来自薯os皂素），并针对HeLa，CaSki和ViBo宫颈外膜癌细胞进行测试。这些化合物对肿瘤细胞和人淋巴细胞显示出低细胞毒性值，表明主要的细胞死亡过程可能不是坏死。重要的是，这些化合物对肿瘤细胞的抗增殖活性并不影响外周血淋巴细胞的增殖潜能。