(1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol | 220497-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol
• 英文别名: (1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride salt；(1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride；(1S,2R,3S,4S)-2,3-dihydroxy-4-(hydroxymethyl)-1-aminocyclopentane hydrochloride；(1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol;hydrochloride
• CAS: 220497-88-1
• 化学式: C₆H₁₃NO₃*ClH
• 分子量: 183.635
• InChiKey: BLTXEPQZAMUGID-VKYWDCQCSA-N

物化性质

• 熔点：
  125.4 °C
• 密度：
  1.2361 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  11
• 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：
  86.7
• 氢给体数：
  5
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38

SDS

Name:	(1S 2R 3S 4S)-2 3-Dihydroxy-4-(Hydroxymethyl)-1-Aminocyclopentane Material Safety Data Sheet
Synonym:	None Known
CAS:	220497-88-1

Section 1 - Chemical Product MSDS Name:(1S 2R 3S 4S)-2 3-Dihydroxy-4-(Hydroxymethyl)-1-Aminocyclopentane Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
220497-88-1	(1S,2R,3S,4S)-2,3-Dihydroxy-4-(Hydroxy	95%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 220497-88-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 125.4 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H14ClNO3
Molecular Weight: 183.63

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 220497-88-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1S,2R,3S,4S)-2,3-Dihydroxy-4-(Hydroxymethyl)-1-Aminocyclopentane Hydrochloride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 220497-88-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 220497-88-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 220497-88-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol 在 18-冠醚-6 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 四丁基氟化铵 、 sodium methylate 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 113.58h， 生成 (+/-)-5-hydroxymethylcyclopent-2-enone
  参考文献：
  名称：

  三氟化二乙氨基硫在制备碳环核苷合成子中的用途

  摘要：

  三氟二乙基氨基硫（DAST）将受保护的氨基三醇（4）转化为含氟化合物（8）和（10）。相同的试剂将醇（9）转化为化合物（10），（5）和（11），并将叠氮基醇（15）转化为氟叠氮化物（16）和（19）。氟化化合物（5），（8）和（16）是用于氟碳环核苷的有用的合成子。讨论了相邻基团对某些DAST反应过程的影响。

  DOI：

  10.1039/p19880000549
• 作为产物：
  描述：

  Methyl 4β-Amino-2α,3α-dihydroxy-1β-cyclopentanecarboxylate Hydrochloride 在 calcium borohydride 、 水 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 18.0h， 生成 (1S,2R,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol
  参考文献：
  名称：

  （±）4β-氨基-2α，3α-二羟基-1β-环戊烷甲醇盐酸盐。碳环核呋喃糖胺用于碳环核苷的合成。

  摘要：

  碳环核呋喃糖胺是合成碳环核糖核苷的关键中间体，是通过内酰胺2-氮杂双环[2.2.1] hept5-ene-3-one的简便方法合成的。

  DOI：

  10.1016/s0040-4039(01)82898-7

文献信息

• [EN] AZO-SUBSTITUTED PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS<br/>[FR] DÉRIVÉS DE PYRIDINE ET PYRIMIDINE SUBSTITUÉES PAR AZO ET LEUR UTILISATION DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：SCHERING CORP

  公开号：WO2010022126A1

  公开（公告）日：2010-02-25

  The present invention provides compounds of Formula (I): (Chemical formula should be inserted here as it appears on abstract in paper form) (I) and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein wherein each of R, R1, X, Y, Z, R2, R3, R4, R5, R6, R7, R8, R9, R18, R19, and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing dieases or disorders such as viral infections and virus-related disorders.

  本发明提供了化合物的结构式（I）：（化学式应如纸质摘要中所示），以及该化合物的互变异构体、同分异构体和酯，以及该化合物的药用盐、溶剂合物和前药，其中R、R1、X、Y、Z、R2、R3、R4、R5、R6、R7、R8、R9、R18、R19和n中的每个均独立选择并在此定义。还提供了包含这些化合物的组合物。本发明的化合物作为HCV的抑制剂具有有效性，并且在单独使用或与其他治疗剂一起使用时，对治疗或预防病毒感染和与病毒相关的疾病或紊乱具有用处。
• Exploring Unconventional SAM Analogues To Build Cell‐Potent Bisubstrate Inhibitors for Nicotinamide <i>N</i> ‐Methyltransferase
  作者：Iredia D. Iyamu、Jonah Z. Vilseck、Ravi Yadav、Nicholas Noinaj、Rong Huang

  DOI：10.1002/anie.202114813

  日期：2022.4.11

  selective nicotinamide N-methyltransferase (NNMT) bisubstrate inhibitor, II399, was discovered by structure-based optimization by introducing unconventional S-adenosyl-L-methionine (SAM) mimics. The inhibition mechanism studies and crystal structure of the NNMT–II399 complex confirm its engagement with both SAM and substrate binding sites. II399 potently inhibits the methyltransferase activity of NNMT in

  第一个细胞有效的选择性烟酰胺N-甲基转移酶 (NNMT) 双底物抑制剂II399是通过引入非常规的S-腺苷-L-甲硫氨酸 (SAM) 模拟物通过基于结构的优化发现的。 NNMT- II399复合物的抑制机制研究和晶体结构证实了其与 SAM 和底物结合位点的结合。 II399有效抑制细胞中 NNMT 的甲基转移酶活性。
• AZO-SUBSTITUTED PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS
  申请人：Kwong Cecil D.

  公开号：US20110286964A1

  公开（公告）日：2011-11-24

  The present invention provides compounds of Formula (I): (Chemical formula should be inserted here as it appears on abstract in paper form) (I) and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein each of R, R 1 , X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 18 , R 19 , and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing dieases or disorders such as viral infections and virus-related disorders.

  本发明提供了式(I)的化合物：（将在论文中以纸质形式出现的化学式插入此处）（I）及其互变异构体、异构体和酯类，以及所述化合物的药学上可接受的盐、溶剂化物和前药，其中每个R、R1、X、Y、Z、R2、R3、R4、R5、R6、R7、R8、R9、R18、R19和n均是独立选择并如所定义。还提供了包含此类化合物的组合物。本发明的化合物是HCV抑制剂，可用于治疗或预防病毒感染和与病毒相关的疾病或障碍，单独或与其他治疗剂一起使用。
• INHIBITORS OF IRAK4 ACTIVITY
  申请人：SEGANISH W. Michael

  公开号：US20150299224A1

  公开（公告）日：2015-10-22

  The present invention relates to compounds which modulate interleukin-1 (IL-1) receptor-associated kinase 4 (IRAK4) and are useful in the prevention or treatment of inflammatory, cell proliferative and immune-related conditions and diseases. Specifically, provided herein are inhibitors of IRAK4 of Formula I and pharmaceutical compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

  本发明涉及调节白细胞介素-1（IL-1）受体相关激酶4（IRAK4）的化合物，可用于预防或治疗炎症、细胞增殖和免疫相关的疾病和病症。具体地，本文提供了IRAK4抑制剂I式化合物和包含这些抑制剂的药物组合物，以及使用这些抑制剂的方法来治疗IRAK4介导或相关的疾病或病症。
• [EN] INHIBITORS OF NICOTINAMIDE N-METHYL TRANSFERASE (NNMT)<br/>[FR] INHIBITEURS DE NICOTINAMIDE N-MÉTHYL TRANSFÉRASE (NNMT)
  申请人：UNIV LEIDEN

  公开号：WO2022211627A1

  公开（公告）日：2022-10-06

  This invention relates to compounds that are useful as inhibitors, in particular as inhibitors of NicotinamideN-methyltransferase (NNMT), and formulations composing such compounds. The compounds and formulations may be used as a medicament, for example in the treatment of cancer, metabolic disease, or neurodegenerative disease. The compounds may be of formula (I).

  本发明涉及一种作为抑制剂的化合物，特别是作为烟酰胺N-甲基转移酶（NNMT）的抑制剂，以及由这种化合物组成的制剂。这些化合物和制剂可用作药物，例如用于治疗癌症、代谢性疾病或神经退行性疾病。这些化合物可以是公式（I）的化合物。