3,4-二氢-2H-硫代色烯-4-胺 | 93192-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 中文名称: 3,4-二氢-2H-硫代色烯-4-胺
• 英文名称: 3,4-dihydro-2H-thiochromen-4-ylamine
• 英文别名: thiochroman-4-ylamine；thiochroman-4-amine；(+/-)-Thiochroman-4-ylamin；Thiochroman-4-ylamin；4-amino-3,4-dihydro-1H-benzothiopyran；(+/-)thiochroman-4-ylamine；3,4-dihydro-2H-thiochromen-4-amine
• CAS: 93192-72-4
• 化学式: C₉H₁₁NS
• mdl: MFCD00297135
• 分子量: 165.259
• InChiKey: XMWQQTMIZMZZHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  261.6±39.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,4-Dihydro-2H-thiochromen-4-amine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3,4-Dihydro-2H-thiochromen-4-amine
CAS number: 93192-72-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H11NS
Molecular weight: 165.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-氯嘌呤核苷 、 3,4-二氢-2H-硫代色烯-4-胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (2R,3R,4S,5R)-2-[6-(3,4-dihydro-2H-thiochromen-4-ylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
  参考文献：
  名称：

  N6-Substituted adenosine receptor agonists: potential antihypertensive agents

  摘要：

  Adenosine is known to exert a wide range of pharmacological effects including hypotension. This effect of adenosine suggested that modified analogues of adenosine might provide useful antihypertensive agents. Thus, we prepared a series of novel N6-benzocycloalkyladenosines and studied their receptor binding and antihypertensive activity. The structure-activity relationship study shows that the adenosine analogues having the hydrophobic phenyl moiety one carbon away from the C6-nitrogen have modest affinity and selectivity for the A1 receptor, whereas those with the phenyl moiety two carbons away from the C6-nitrogen have excellent affinity and selectivity for the A1 receptor. Many of these analogues showed excellent antihypertensive activity with a wide range of effects on heart rate. There is no direct correlation between the receptor binding affinities and antihypertensive activity; however, it is more closely associated with A1 than A2 affinity. The bradycardic effect of these agonists seems to be due to the A1 affinity. From this set, compound 3 was further evaluated in secondary antihypertensive screens. It lowered the blood pressure dose dependently with effects lasting for over 20 h following administration of a 30 mg/kg dose. Compound 3 was also effective in lowering blood pressure in a renal hypertensive rat model. Thus, appropriately modified N6-substituted adenosines represent a novel class of antihypertensive agents.

  DOI：

  10.1021/jm00107a025
• 作为产物：
  描述：

  Thiochroman-4-on-oxim 在 溶剂黄146 、 锌 作用下， 生成 3,4-二氢-2H-硫代色烯-4-胺
  参考文献：
  名称：

  CCXXV。–邻舍系列研究。第四部分。苯甲酰胺基联苯戊四烯的四种立体异构体氧化物

  摘要：

  DOI：

  10.1039/jr9310001692

文献信息

• Mechanism-Based Inhibitors of the Human Sirtuin 5 Deacylase: Structure-Activity Relationship, Biostructural, and Kinetic Insight
  作者：Nima Rajabi、Marina Auth、Kathrin R. Troelsen、Martin Pannek、Dhaval P. Bhatt、Martin Fontenas、Matthew D. Hirschey、Clemens Steegborn、Andreas S. Madsen、Christian A. Olsen

  DOI：10.1002/anie.201709050

  日期：2017.11.20

  The sirtuin enzymes are important regulatory deacylases in a variety of biochemical contexts and may therefore be potential therapeutic targets through either activation or inhibition by small molecules. Here, we describe the discovery of the most potent inhibitor of sirtuin 5 (SIRT5) reported to date. We provide rationalization of the mode of binding by solving co‐crystal structures of selected inhibitors

  sirtuin酶在各种生化环境中是重要的调节性去酰基化酶，因此可能通过小分子的激活或抑制而成为潜在的治疗靶标。在这里，我们描述了迄今为止报道的最有效的sirtuin 5（SIRT5）抑制剂的发现。通过解决与人类和斑马鱼SIRT5复杂的选定抑制剂的共晶体结构，我们提供了结合模式的合理化方法，这为进一步优化具有更多“类药物”性质的抑制剂提供了见识。重要的是，酶动力学评估显示出缓慢，紧密的抑制机制，这对于SIRT5而言是前所未有的。当将抑制剂应用于生物学探测机制时，这是重要的信息。
• Substituted aryl 1,4-pyrazine derivatives
  申请人：——

  公开号：US20030144297A1

  公开（公告）日：2003-07-31

  Substituted aryl 1,4-pyrazine derivatives and their use in treating anxiety disorders, depression and stress related disorders are disclosed.

  揭示了替代基苯基1,4-吡嗪衍生物及其在治疗焦虑症、抑郁症和与压力有关的疾病中的用途。
• Ring-Expansion Reaction of Oximes with Aluminum Reductants
  作者：Hidetsura Cho、Yusuke Iwama、Nakako Mitsuhashi、Kenji Sugimoto、Kentaro Okano、Hidetoshi Tokuyama

  DOI：10.3390/molecules17067348

  日期：——

  The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained

  研究了杂环酮肟和碳环酮肟与几种还原剂如 AlHCl2、AlH3（铝烷）、LiAlH4、LiAlH(OtBu)3 和 (MeOCH2CH2O)2AlH2Na（Red-Al）的扩环反应。在还原剂中，环戊基甲基醚 (CPME) 中的 AlHCl2 (LiAlH4:AlCl3 = 1:3) 已被发现是适合该反应的试剂，并且重排的环状仲胺以良好到极好的收率获得。
• [EN] THIOUREA COMPOUNDS AND THEIR USE AS INHIBITORS OF SIRT2 OR SIRT5<br/>[FR] COMPOSÉS À BASE DE THIOURÉE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE SIRT2 OU SIRT5
  申请人：UNIV CORNELL

  公开号：WO2014197775A1

  公开（公告）日：2014-12-11

  A compound useful as a Sirt2 or Sirt5 inhibitor having the formula (1) wherein: R1 is a hydrocarbon group having at least two carbon atoms connected by carbon-carbon bonds, wherein said hydrocarbon group is optionally endcapped by a neutral or anionic oxygen-containing group; R2a, R2b, and R2c are independently selected from hydrogen atom and hydrocarbon groups; X0, X1, X2, and X3 are independently selected from -(CH2)n-, -NR5-, -O-, -S-, and a bond, wherein n represents 1, 2, or 3, provided that at least one of X0-X3 is -(CH2)n-; and R3 and R4 are independently selected from the group consisting of hydrogen atom, hydrocarbon groups, biological groups, and protecting groups. Also described are pharmaceutical compositions of the inhibiting compounds, and methods of treatment by administration of the inhibiting compounds.

  一种作为Sirt2或Sirt5抑制剂有用的化合物，其化学式为(1)，其中：R1是一个碳-碳键连接的至少有两个碳原子的碳氢基团，该碳氢基团可选择地由一个中性或阴离子氧含基团端部封端；R2a、R2b和R2c分别选自氢原子和碳氢基团；X0、X1、X2和X3分别选自-(CH2)n-、-NR5-、-O-、-S-和一个键，其中n表示1、2或3，前提是X0-X3中至少有一个是-( )n-；R3和R4分别选自氢原子、碳氢基团、生物基团和保护基团。还描述了这些抑制化合物的药物组合物，以及通过给予这些抑制化合物进行治疗的方法。
• Optically Active Amines by Enzyme-Catalyzed Kinetic Resolution
  作者：Klaus Ditrich

  DOI：10.1055/s-2008-1078451

  日期：2008.7

  Chiral amines are resolved by an enzyme-catalyzed kinetic resolution. Key steps are the selective acylation of one enantiomer with isopropyl methoxyacetate, separation of the resulting amide from the unreacted antipode, and finally amide hydrolysis. The process proceeds with excellent selectivity and is highly flexible with regard to substrates.

  手性胺通过酶催化动力学拆分进行拆分。关键步骤是用甲氧基乙酸异丙酯选择性酰化一种对映体，将所得酰胺与未反应的对映体分离，最后是酰胺水解。该过程以优异的选择性进行，并且对于基材具有高度的灵活性。