去氧野艽霉素盐酸盐 | 73285-50-4

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 去氧野艽霉素盐酸盐
• 英文名称: 1-deoxynojirimycin hydrochloride
• 英文别名: 1,5-dideoxy-1,5-imino-D-glucitol hydrochloride；(2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride；deoxynojirimycin hydrochloride；D-deoxynojirimycin hydrochloride；D-DNJ·HCl；DNJ HCl；(2R,3R,4R,5S)-2-(hydroxymethyl)piperidin-1-ium-3,4,5-triol;chloride
• CAS: 73285-50-4
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: ZJIHMALTJRDNQI-VFQQELCFSA-N

物化性质

• 熔点：
  195-196°C
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  6
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P280,P301+P312,P302+P352+P312,P304+P340+P312
• 危险性描述：
  H302,H312,H332
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1-Deoxynojirimycin hydrochloride
CAS-No. : 73285-50-4

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 1,5-Dideoxy-1,5-imino-D-sorbitolhydrochloride
Formula : C6H13NO4 · HCl
Molecular Weight : 199,63 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

1-Deoxynojirimycin hydrochloride (Duvoglustat hydrochloride) 是一种口服有效的 α-葡萄糖苷酶抑制剂。这种化合物能够预防餐后血糖升高，有助于糖尿病的管理，并具有降血糖、减肥和抗病毒的作用。

体内研究

在实验中，1-Deoxynojirimycin hydrochloride (Duvoglustat hydrochloride) 显示出显著的减肥效果（20-80 mg/kg，静脉注射，连续四周）。它通过激活骨骼肌中的胰岛素信号 PI3K/AKT 途径，显著改善了 db/db 鼠的胰岛素敏感性。

实验结果

• 动物模型：db/db 鼠
• 剂量：20, 40, 80 mg/kg
• 给药方式：静脉注射；连续四周
• 结果：
  • 显著减轻体重、降低血糖和血清胰岛素水平；
  • 改善葡萄糖耐受性和胰岛素敏感性。

反应信息

• 作为反应物：
  描述：

  去氧野艽霉素盐酸盐 在 Amberlite HPR₅₅₀ OH 作用下， 以 甲醇 为溶剂， 以2.8 mg的产率得到1-脱氧野尻霉素
  参考文献：
  名称：

  侧链构象对糖苷酶抑制剂活性的影响

  摘要：

  报告了抑制剂侧链构象的预组织可以有利地影响糖苷酶抑制的第一个实验证明。通过在 C6 上策略性地安装甲基，发现具有gauche,gauche侧链构象的甘露糖配置的亚氨基糖是比 1-脱氧甘露尻霉素强 27 倍的抑制剂。

  DOI：

  10.1002/anie.202217809
• 作为产物：
  描述：

  1-脱氧野尻霉素 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到去氧野艽霉素盐酸盐
  参考文献：
  名称：

  量化哌啶模型系统中常见碳水化合物保护基的电子效应

  摘要：

  进行了羟基哌啶中保护基的取代基作用的研究，并将其与糖基化化学中的电子作用进行了比较。1-脱氧野尻霉素，1-脱氧的氮杂-糖类似物d葡萄糖，用作碳水化合物模型，并与最常见的糖类保护基团保护。环杂原子上正电荷的不同稳定度通过p K a测量确定。保护基在哌啶离子不稳定后，可以通过以下方式进行分级：苯甲酰基≥乙酰基≫4,6-‐ O‐苄基>苄基≈甲基> H> 3,6-脱水>叔ter-丁基二甲基甲硅烷基。发现具有不同电子特性的保护基的观察到的结果与“武装撤防”的概念一致。比较3-羟基-6-羟甲基哌啶的苄基和苯甲酰差向异构体的p K a，可以看出轴向差向异构体中哌啶离子的稳定性增加。轴向和赤道差向异构体之间的差异在苄基化合物中比在苯甲酰化哌啶中更大。

  DOI：

  10.1002/chem.201002313

文献信息

• Radical Cyclization in Heterocycle Synthesis. Part 9: A Novel Synthesis of Aminocyclitols and Related Compounds via Stannyl Radical Cyclization of Oxime Ethers Derived from Sugars
  作者：Toshiko Kiguchi、Kazumi Tajiri、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/s0040-4020(00)00545-7

  日期：2000.8

  Stannyl radical addition–cyclization of oxime ethers derived from d-glucose, d-galactose, and d-xylose proceeded smoothly to afford alkoxyamino alcohols which were effectively converted into two types of glycosidase inhibitors or its candidates such as aminocyclitols, 1-deoxynojirimycin, and 1-deoxygalactostatin via reductive ring-expansion of trans alkoxyamino alcohols.

  斯坦尼基自由基加成反应-衍生自d-葡萄糖，d-半乳糖和d-木糖的肟醚的环化反应顺利进行，得到的烷氧基氨基醇可有效地转变为两种类型的糖苷酶抑制剂或其候选物，例如氨基环糖醇，1-脱氧野oji霉素和1-脱氧半乳糖抑素通过反式烷氧基氨基醇的还原性扩环而形成。
• DEOXYNOJIRIMYCIN DERIVATIVES AND METHODS OF THEIR USING
  申请人：EMERGENT VIROLOGY LLC

  公开号：US20160221993A1

  公开（公告）日：2016-08-04

  The present application provide novel iminosugars and their use in treatment of viral infections, such as Dengue infection and Influenza A infection. The present inventors discovered certain deoxynojirimycin derivatives may be effective against one or more viruses, which may be, for example, a Dengue virus and/or a virus belonging to the Orthomyxoviridae family, such as an Influenza A virus. In particular, such deoxynojirimycin derivatives may be useful for treating a disease or condition caused by or associated with one or more viruses. In certain embodiments, the deoxynojirimycin derivatives may increase a survival rate or probability for a subject infected with one or more viruses, which may be, for example, a Dengue virus and/or a virus belonging to the Orthomyxoviridae family, such as an Influenza A virus.

  该申请提供了新型亚胺糖及其在治疗病毒感染方面的用途，例如登革热感染和甲型流感感染。本发明者发现某些脱氧诺吉霉素衍生物可能对一种或多种病毒有效，例如登革病毒和/或属于流感病毒科的病毒，如甲型流感病毒。特别是，这些脱氧诺吉霉素衍生物可能有助于治疗由一种或多种病毒引起或相关的疾病或症状。在某些实施方式中，这些脱氧诺吉霉素衍生物可能提高受感染的个体的存活率或概率，例如登革病毒和/或属于流感病毒科的病毒，如甲型流感病毒。
• Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin
  作者：Martina De Angelis、Carla Sappino、Emanuela Mandic、Marianna D’Alessio、Maria Grazia De Dominicis、Sara Sannino、Ludovica Primitivo、Paolo Mencarelli、Alessandra Ricelli、Giuliana Righi

  DOI：10.1016/j.tet.2020.131837

  日期：2021.1

  approach for producing piperidine iminosugars has been developed employing a common optically active precursor. The key steps of the synthetic pathway are the double diastereoselection in the asymmetric dihydroxylation of the suitable chiral vinyl epoxy ester and the regio- and stereospecific opening of the epoxide ring with azide. The synthesis of two piperidine iminosugars, 1-deoxy-D-altronojirimycin and

  已经开发了使用常见的光学活性前体来生产哌啶亚氨基糖的立体发散方法。合成途径的关键步骤是合适的手性乙烯基环氧酯的不对称二羟基化中的双非对映异构，以及叠氮化物对环氧环的区域和立体有择的开环。两种相关的路线可实现两种哌啶亚氨基糖的合成，即1-脱氧-D-altroojirimycin和1-脱氧-D-nojirimycin。
• Probing the Inhibitor versus Chaperone Properties of sp2-Iminosugars towards Human β-Glucocerebrosidase: A Picomolar Chaperone for Gaucher Disease
  作者：Teresa Mena-Barragán、M. García-Moreno、Alen Sevšek、Tetsuya Okazaki、Eiji Nanba、Katsumi Higaki、Nathaniel Martin、Roland Pieters、José Fernández、Carmen Mellet

  DOI：10.3390/molecules23040927

  日期：——

  nature of the nonglycone substituent has been synthesized and assayed for their inhibition properties towards commercial glycosidases. On the basis of their affinity and selectivity towards GH1 β-glucosidases, reducing and nonreducing bicyclic derivatives having a hydroxylation profile of structural complementarity with d-glucose and incorporating an N′-octyl-isourea or -isothiourea segment were selected

  合成了一系列在还原性或非还原性、构型模式（d-葡萄糖或 l-ido）、糖基骨架的结构和非糖基取代基的性质方面不同的 sp2-亚氨基糖糖模拟物，并对其抑制进行了分析对商业糖苷酶的特性。根据它们对 GH1 β-葡萄糖苷酶的亲和力和选择性，选择具有与 d-葡萄糖结构互补的羟基化特征并结合 N'-辛基-异脲或 -异硫脲片段的还原性和非还原性双环衍生物，以进一步评估它们的对人葡糖脑苷脂酶 (GCase) 的抑制/伴侣潜力。1-脱氧野尻霉素 (DNJ) 相关的非还原性偶联物比还原性偶联物表现出更强的 GCase 抑制剂，并在携带神经病性 G188S/G183W 突变的戈谢成纤维细胞中表现出强大的伴侣能力，异硫脲衍生物确实是报道的最有效的伴侣候选物之一迄今为止（20 pM 时活性增强 70%）。在最佳浓度下，四种选定的化合物促进了 3 倍以上的突变 GCase 活性增强；然而，与还原衍生物相比，抑制剂/
• Method for the treatment of Pompe disease using 1-deoxynojirimycin and derivatives
  申请人：Mugrage Benjamin

  公开号：US20060264467A1

  公开（公告）日：2006-11-23

  The present invention provides a method for increasing the activity of a mutant or wild-type α-glucosidase enzyme in vitro and in vivo by contacting the enzyme with a specific pharmacological chaperone which is a derivative of 1-deoxynojirimycin. The invention also provides a method for the treatment of Pompe disease by administration of chaperone small molecule compound which is a derivative of 1-deoxynojirimycin. The 1-deoxynojirimycin derivative is substituted at the N or C1 position. Combination therapy with replacement α-glucosidase gene or enzyme is also provided.

  本发明提供了一种通过将酶与一种特定的药理伴侣接触来增加体外和体内突变型或野生型α葡萄糖苷酶酶活性的方法，该药理伴侣是1-去氧诺吉霉素的衍生物。该发明还提供了一种通过给予1-去氧诺吉霉素衍生物的伴侣小分子化合物来治疗庞贝病的方法。1-去氧诺吉霉素衍生物在N或C1位置被取代。还提供了与替代α葡萄糖苷酶基因或酶的联合治疗方法。