methyl α-D-manno-heptopyranosidurononitrile | 225243-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-manno-heptopyranosidurononitrile
• 英文别名: methyl 6-deoxy-6-cyano-α-D-mannopyranoside；methyl 6-cyano-6-deoxy-α-D-mannopyranoside；2-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]acetonitrile
• CAS: 225243-28-7
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: DYUHUJRRDJPOAS-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α-D-manno-heptopyranosidurononitrile 在 氢气 作用下， 以 甲醇 、 水 为溶剂， 以10%的产率得到methyl 7-amino-6,7-dideoxy-α-D-manno-heptopyranoside
  参考文献：
  名称：

  6-磷酸甘露糖类似物的合成及其作为血管生成调节剂的作用

  摘要：

  实用价值低：据报道，一种有效的方法使用关键的环状硫酸盐中间体合成了在C-6位置修饰的甘露糖-6-磷酸酯（M6P）类似物。这些类似物代表了第一个已知的血管生成单糖效应子。此外，此处报道的结果证实了M6P受体参与了血管形成。

  DOI：

  10.1002/cmdc.201100293
• 作为产物：
  描述：

  methyl 2,3,4-tribenzoyl-6-cyano-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 生成 methyl α-D-manno-heptopyranosidurononitrile
  参考文献：
  名称：

  Anti-(retro)viral conjugates of saccharides and acetamidino or guanidino compounds

  摘要：

  糖苷和乙酰胺基甲基或胍基化合物的共轭物，其化学式为：其中A为CH3或NH2；X为线性或支链的C1-C8烷基链，可含有羟基、氨基和/或羰基基团；n为1到6的整数，Sac为单糖或寡糖的残基，但当A为NH2且X为-(CH2)3—CH(NH2)—C(=O)-时，单糖残基在位置1不被取代，当Sac为寡糖残基时，n为2到6的整数，这些化合物可用作抗病毒药物，特别是作为抗逆转录病毒药物，可单独使用或与用于艾滋病治疗的其他化合物一起使用，如AZT和/或蛋白酶抑制剂，用于治疗HIV感染、艾滋病及艾滋病表现，如卡波西肉瘤。特别优选的化合物是氨基糖苷-精氨酸共轭物，其中糖苷是天然的氨基糖苷抗生素，如卡那霉素、庆大霉素和新霉素，这些抗生素与精氨酸残基共轭。

  公开号：

  US06642365B1

文献信息

• NOVEL USES OF D-MANNOPYRANOSE DERIVATIVES ACTIVATING ANGIOGENESIS
  申请人：Montero Jean-Louis

  公开号：US20110124558A1

  公开（公告）日：2011-05-26

  The invention relates to the use of certain derivatives of D-mannopyranoside for controlling angiogenesis. These compounds have a pro-angiogenic activity, and can particularly be used for preparing a pharmaceutical composition for treating cardiovascular diseases or for treating muscular atrophy. The invention also relates to certain D-mannopyranoside derivatives, to a pharmaceutical or cosmetic composition containing said derivatives, and to the use of such a cosmetic composition for preventing and/or treating hair loss.

  该发明涉及利用某些D-甘露聚糖衍生物来控制血管生成。这些化合物具有促血管生成活性，特别适用于制备用于治疗心血管疾病或肌肉萎缩的药物组合物。该发明还涉及某些D-甘露聚糖衍生物，含有该衍生物的药用或化妆品组合物，以及利用此类化妆品组合物预防和/或治疗脱发。
• NOVEL USES OF D-MANNOPYRANOSE DERIVATIVES
  申请人：Monteron Jean-Louis

  公开号：US20110112044A1

  公开（公告）日：2011-05-12

  The invention relates to the use of mannose-6-phosphate (M6P) and of certain derivatives thereof for controlling angiogenesis and ligament regeneration and/or cartilage reconstruction. The MP6 and certain derivatives thereof can particularly be used for preparing a pharmaceutical composition used for ligament regeneration and/or cartilage reconstruction.

  该发明涉及利用甘露糖-6-磷酸（M6P）及其某些衍生物来控制血管生成、韧带再生和/或软骨重建。M6P及其某些衍生物特别可用于制备用于韧带再生和/或软骨重建的药物组合物。
• [EN] ANTI-(RETRO)VIRAL CONJUGATES OF SACCHARIDES AND ACETAMIDINO OR GUANIDINO COMPOUNDS<br/>[FR] CONJUGUES ANTI-RETROVIRAUX DE SACCHARIDES ET DE COMPOSES ACETAMIDINO OU GUANIDINO
  申请人：YEDA RES & DEV

  公开号：WO2000039139A1

  公开（公告）日：2000-07-06

  Conjugates of saccharide and an acetamidino- or guanidino- compounds of formula (I), wherein A is CH3 or NH2; X is a linear or branched C1-C8 alkyl chain optionally containing hydroxy, amino and/or oxo groups; n is an integer from 1 to 6, and Sac is the residue of a mono- or oligo-saccharide are useful as antiviral, particularly as antiretroviral, agents, and can be used either alone or together with other compounds used in AIDS treatment such as AZT and/or protease inhibitors, for the treatment of HIV-infection, AIDS and manifestations of AIDS such as Kaposi sarcoma. Particularly preferred compounds are aminoglycoside-arginine conjugates in which the saccharide is a natural aminoglycoside antibiotic such as kanamycin, gentamycin and neomycin that is conjugated to arginine residues.

  糖苷的共轭物和式（I）的乙酰胺基或鸟氨酸基化合物，其中A为CH3或NH2; X是一个线性或支链的C1-C8烷基链，可选包含羟基，氨基和/或氧代基; n是1至6的整数，Sac是单糖或寡糖的残基，可用作抗病毒药物，特别是作为抗逆转录病毒药物，并且可以单独或与用于治疗艾滋病的其他化合物一起使用，例如AZT和/或蛋白酶抑制剂，用于治疗HIV感染，艾滋病和艾滋病的表现，例如卡波西肉瘤。特别优选的化合物是氨基糖苷-精氨酸共轭物，其中糖苷是天然的氨基糖苷抗生素，例如卡那霉素，庆大霉素和新霉素，与精氨酸残基结合。
• Synthesis of 6,7-dideoxy-7-isothiocyanatoheptoses: stable fully unprotected monosaccharide isothiocyanates
  作者：Juan Manuel Benito、Carmen Ortiz Mellet、José Manuel Garcı́a Fernández

  DOI：10.1016/s0008-6215(99)00273-6

  日期：1999.1

  Methyl 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco (manno)(galacto)-heptopyranosides have been synthesized in four steps by homologation of the respective methyl hexopyranosides via the corresponding heptopyranosydurononitriles. Neither intra- nor intermolecular thiocarbamate formation was observed, even under rather strenuous acidic or basic conditions. The reducing derivative 6,7-dideoxy-7-isothiocyanato-alpha-D-gluco-heptopyranose was also a stable compound in aqueous solution in the absence of base. Formation of a six-membered intramolecular cyclic thiocarbamate was achieved in DMF solution in the presence of triethylamine. The title compounds are the first examples of stable fully unprotected monosaccharide isothiocyanates.
• ANTI-(RETRO)VIRAL CONJUGATES OF SACCHARIDES AND ACETAMIDINO OR GUANIDINO COMPOUNDS
  申请人：YEDA RESEARCHAND DEVELOPMENT COMPANY, LTD.

  公开号：EP1140958A1

  公开（公告）日：2001-10-10