贝那米星B | 116249-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 中文名称: 贝那米星B
• 英文名称: benanomicin B
• 英文别名: pradimicin C；(2R)-2-[[(5S,6S)-5-[(2S,3R,4S,5S,6R)-5-amino-3-hydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-1,6,9,14-tetrahydroxy-11-methoxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carbonyl]amino]propanoic acid
• CAS: 116249-66-2
• 化学式: C₃₉H₄₂N₂O₁₈
• 分子量: 826.765
• InChiKey: IHIIRQILYAXIOH-NUVDETJMSA-N

物化性质

• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  335
• 氢给体数：
  11
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  贝那米星B 在 盐酸 、 乙酸酐 作用下， 生成 methyl 4,6-dideoxy-4-amino-D-galactopyranoside
  参考文献：
  名称：

  The structure of pradimicins A, B and C: a novel family of antifungal antibiotics

  摘要：

  DOI：

  10.1021/jo00272a013

文献信息

• Antifungal activities of pradimicin derivatives modified at C4'-amino group.
  作者：HAJIME KAMACHI、SATSUKI OKUYAMA、MINORU HIRANO、SHINJI MASUYOSHI、MASATAKA KONISHI、TOSHIKAZU OKI

  DOI：10.7164/antibiotics.46.1246

  日期：——

  In order to explore potent derivatives of pradimicins (PRMs), modification of their C4'-amino group was carried out. 4'-N-Cyano (1, 2), 4'-deamino-4'-nitroguanidino (4), 4'-deamino-4'-ureido (7-9) and 4'-deamino-4'-thioureido (10) derivatives were synthesized by trimethylsilylation of PRMs A and C, followed by condensation with appropriate reagents. 4'-Deamino-4'-guanidino (5) and 4'-deamino-4'-amidino (6) derivatives were synthesized by catalytic hydrogenation of 4 and 2, respectively. 4'-N-Nitroso derivative 3 was prepared by treatment of PRM A with nitrous acid. Among these compounds, the 4'-N-cyano derivative of PRM C (2) exhibited in vitro and in vivo antifungal activities comparable to the parent compounds together with good water-solubility.

  为了探索普拉迪米星（PRMs）的强效衍生物，对其 C4'-氨基进行了修饰。通过对 PRMs A 和 C 进行三甲基硅烷化，然后用适当的试剂缩合，合成了 4'-N-Cyano (1, 2)、4'-deamino-4'-nitroguanidino (4)、4'-deamino-4'-ureido (7-9) 和 4'-deamino-4'-thioureido (10) 衍生物。4'-Deamino-4'-guanidino (5) 和 4'-deamino-4'-amidino (6) 衍生物分别由 4 和 2 催化加氢合成。4'-N-Nitroso 衍生物 3 是用亚硝酸处理 PRM A 而制备的。在这些化合物中，PRM C 的 4'-N-Cyano 衍生物（2）具有与母体化合物相当的体内外抗真菌活性和良好的水溶性。
• New antibiotic N-acetyl-benanomicin B, and the production and uses thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0378126A1

  公开（公告）日：1990-07-18

  As a new compound is now provided N-­acetylbenanomicin B which is useful as an antifungal agent and also as antiviral agent for inhibiting infec­tion of human T-cell with HIV, namely a virus causative of acquired human immunodeficiency syndrome. N-­acetylbenanomicin B may be prepared by acetylation of 4˝-amino group of benanomicin B which is fermentatively produced by a new microorganism, MH193-16F4 strain of actinomycetes.

  现在提供的一种新化合物 N-乙酰苯氨霉素 B 可用作抗真菌剂，也可用作抑制人类 T 细胞感染艾滋病毒（即导致获得性免疫缺陷综合征的病毒）的抗病毒剂。N-acetylbenanomicin B 可以通过乙酰化苯氨霉素 B 的 4˝-氨基来制备，苯氨霉素 B 是由放线菌 MH193-16F4 株这种新微生物发酵产生的。
• Pradimicins L and FL and derivatives thereof
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0479505A1

  公开（公告）日：1992-04-08

  The present invention relates to novel antifungal antibiotics herein designated as pradimicin L and pradimicin FL, and derivatives thereof. Pradimicins L and FL are produced by Actinomadura verrucosospora subsp. neohibisca strain R103-3, ATCC No. 53930.

  本发明涉及新型抗真菌抗生素，在此命名为 Pradimicin L 和 Pradimicin FL 及其衍生物。Pradimicins L和FL由Actinomadura verrucospora subsp.neohibisca菌株R103-3（ATCC编号53930）产生。
• Pradimic acids, amides, and novel pradimicin derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：EP0580480A1

  公开（公告）日：1994-01-26

  The present invention relates to intermediates, pradimic acids and pradimic acid amides of the formula (II) wherein R is OH or NH₂; R¹ is hydrogen or a group of the formula with the proviso that when R is OH, R¹ is not hydrogen; Y is OH or NR²R³; R² is hydrogen or methyl; R³ is hydrogen, C₁₋₅ alkyl, or an amino protecting group; R⁴ is hydrogen, hydroxy protecting group, or β-D-xylosyl. The invention relates also to novel processes for the preparation of pradimic acids and pradimic acid amides, as well as novel pradimicin derivatives prepared therefrom.

  本发明涉及式 (II) 的中间体、普拉底米酸和普拉底米酸酰胺 其中 R 是 OH 或 NH₂；R¹是氢或式中的基团 但当 R 是 OH 时，R¹ 不是氢；Y 是 OH 或 NR²R³；R² 是氢或甲基；R³ 是氢、C₁₋₅ 烷基或氨基保护基；R⁴ 是氢、羟基保护基或β-D-木糖基。 本发明还涉及制备普拉底米酸和普拉底米酸酰胺的新型工艺，以及由此制备的新型普拉底米素衍生物。
• Pradimicin compounds
  申请人：Bristol-Myers Squibb Company

  公开号：EP0584014A1

  公开（公告）日：1994-02-23

  Disclosed are novel pradimicin compounds (I) which possess antifungal activity and, preferably, improved water solubility. The compounds of the invention are prepared by modifying the 4'-amino or 4'-alkylamino moieties of known pradimicin compounds. wherein R¹ is H, methyl, or hydroxymethyl, provided that when R¹ is methyl or hydroxymethyl, the resulting amino acid residue has the D configuration; R² is H or β-D-xylosyl; R³ is H or alkyl; R⁴ is -CN, -NO, or a pharmaceutically acceptable salt thereof.

  本发明公开了具有抗真菌活性的新型普拉提米星化合物 (I)，最好还能提高其水溶性。本发明的化合物是通过修饰已知的普拉迪明化合物的 4'- 氨基或 4'- 烷基氨基而制备的。 其中 R¹ 是 H、甲基或羟甲基，但当 R¹ 是甲基或羟甲基时，所得氨基酸残基具有 D 构型；R² 是 H 或 β-D-木糖基；R³ 是 H 或烷基；R⁴ 是 -CN、-NO、 或其药学上可接受的盐。