2-亚氨基硫烷盐酸盐 | 4781-83-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚氨硫酯类
• 中文名称: 2-亚氨基硫烷盐酸盐
• 中文别名: 2-亚氨基噻烷；2-亚氨基硫杂环戊烷盐酸盐
• 英文名称: 2-iminothiolane hydrochloride
• 英文别名: Traut's reagent；Traut’s reagent；2-iminotetrahydrothiophenehydrochloride；Thiolan-2-ylideneazanium;chloride；thiolan-2-ylideneazanium;chloride
• CAS: 4781-83-3
• 化学式: C₄H₇NS*ClH
• mdl: MFCD00039013
• 分子量: 137.633
• InChiKey: ATGUDZODTABURZ-UHFFFAOYSA-N

物化性质

• 熔点：
  198-201 °C(lit.)
• 溶解度：
  H2O:100 mg/mL
• 稳定性/保质期：
  常温常压下稳定并结晶，具有吸湿性。对空气敏感。熔点为198～201℃。

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2934999090
• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P261,P280,P302+P352,P304+P341,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  本品应密封保存在4℃、干燥且避光的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Iminothiolane HCl
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: 2-Iminothiolane HCl
CAS number: 4781-83-3

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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: C4H7NS.ClH
Molecular weight: 137.6

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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, hydrogen chloride, 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

制备方法与用途

伯胺的硫醇化试剂，在pH值为7至10的情况下，脒键会发生反应生成游离巯基。该试剂适用于制备二硫化物和/或硫醚键连接的共轭物。

反应信息

• 作为反应物：
  描述：

  2-亚氨基硫烷盐酸盐 、 硫酸新霉素 在 5'-GGA CUG GGC GAG AAG UUU AGU CC-3' 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Methods for chemical synthesis of biologically active compounds using supramolecular protective groups and novel compounds obtainable Thereby

  摘要：

  这项发明涉及药物开发和合成化学，特别是基于天然分子制造生物活性化合物。它还涉及新型生物活性化合物，例如氨基糖苷类抗生素，以较纯的位置异构形式存在。

  公开号：

  US20140243280A1
• 作为产物：
  描述：

  S-3-cyanopropyl thioacetate 在 三甲基氯硅烷 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以45%的产率得到2-亚氨基硫烷盐酸盐
  参考文献：
  名称：

  由乙烯基腈温和合成硫醇腈及其环化反应†

  摘要：

  硫代乙酸A的硫醇-烯加成法广泛用于由乙烯基前体合成硫醇，但到目前为止，尚未在非共轭乙烯基腈上进行。使用乙烯基腈时，面临的挑战是选择性进行硫醇-烯加成，同时避免将A亲核加成至腈基。我们发现，只要存在化学引发剂量的A，乙烯基腈在光引发剂的存在下就能选择性地诱导UV诱导的硫醇-烯加成反应。乙烯基基团上可以使用乙烯基，并且使用空间上不受阻碍的乙烯基。相反，当使用位阻乙烯基时，腈的亲核加成是有利的。所制备的硫醇腈在碱性和酸性条件下以及在硅胶存在下均可轻松进行环化反应。这说明了腈对硫醇添加的高反应性。1,2-乙二硫醇B是A的替代试剂，因为它允许在温和的和非酸性的反应条件下将乙烯基腈直接转化为硫醇。

  DOI：

  10.1039/c6ra21948a

文献信息

• Insect control compounds
  申请人：American Cyanamid Company

  公开号：US04004019A1

  公开（公告）日：1977-01-18

  The invention is novel hydrocarbon ethers of aminophenol derivatives, and their use in preventing the proliferation of insects by interfering with their normal development and growth pattern.

  这项发明涉及新颖的氨基酚衍生物的烃醚化合物，以及它们在通过干扰昆虫正常发育和生长模式来防止昆虫繁殖方面的应用。
• Synthesis and antiproliferative activities of doxorubicin thiol conjugates and doxorubicin-SS-cyclic peptide
  作者：Shaban Darwish、Neda Sadeghiani、Shirley Fong、Saghar Mozaffari、Parinaz Hamidi、Thimanthi Withana、Sun Yang、Rakesh Kumar Tiwari、Keykavous Parang

  DOI：10.1016/j.ejmech.2018.10.042

  日期：2019.1

  comparable cytotoxicity when compared to Dox in HEK-293, HT-1080, and CCRF-CEM cells after 24 h and 72 incubation, presumably because of higher activity and retention of the compounds in these cells. Furthermore, Dox-SS-[C(WR)4K] showed significantly higher cytotoxic activity in HEK-293, HT-1080, and SKOV-3 cells when compared with Dox after 72 h incubation. Dox-SS-Pyr exhibited higher cellular uptake than Dox-SS-[C(WR)4K]

  药物外排引起的心肌毒性和耐药性是基于多柔比星 (Dox) 的化疗的主要局限性。Dox 结构修饰可用于开发具有改进生物学特性的缀合物，例如抗增殖活性和更高的细胞保留。因此，Dox 硫醇缀合物、Dox 硫醇 (Dox-SH)、硫醇反应性 Dox-SS-吡啶（SS = 二硫化物）和 Dox-SS-细胞穿透环肽 Dox-SS-[C(WR) 4 K]，被合成。Dox 与 Traut 试剂反应生成 Dox-SH。通过与二硫代二吡啶反应活化硫醇基团，得到相应的Dox-SS-吡啶(Dox-SS-Pyr)。含有半胱氨酸残基的环状细胞穿透肽 [C(WR) 4K] 是使用 Fmoc 固相策略制备的。Dox-SS-Py 与 [C(WR) 4 K]中半胱氨酸的游离巯基反应，生成 Dox-SS-[C(WR) 4 K] 作为 Dox 环肽缀合物。在人胚胎肾 (HEK-293)、人卵巢癌 (SKOV-3)、人纤维肉瘤 (HT-1080)
• Cyclic peptide conjugate of curcumin and doxorubicin as an anticancer agent
  作者：Shaban Darwish、Saghar Mozaffari、Keykavous Parang、Rakesh Tiwari

  DOI：10.1016/j.tetlet.2017.10.065

  日期：2017.12

  curcumin-doxorubicin conjugated cyclic peptide scaffold to improve the solubility of curcumin and create a conjugate containing two anticancer agents. A solid-phase Fmoc/tBu solid phase methodology was used to synthesize a cell-penetrating nuclear targeting peptide with free thiol and amine groups, which was coupled with the activated doxorubicin (Dox) and curcumin, affording Dox-peptide-curcumin conjugate (DPCC)

  姜黄素的疏水性为其在抗癌治疗中的应用创造了障碍。在这里，我们合成了姜黄素-阿霉素偶联的环状肽支架，以提高姜黄素的溶解度并创建包含两种抗癌剂的偶联物。使用固相Fmoc / tBu固相方法合成具有游离巯基和胺基的穿透细胞的核靶向肽，然后将其与活化的阿霉素（Dox）和姜黄素偶联，得到Dox-肽-姜黄素共轭物（DPCC） ）（10）。在人白血病癌细胞（CCRF-CEM），人卵巢癌细胞（SKOV-3）和正常肾细胞系（LLCPK）中评估了缀合物的抗增殖活性。环肽-阿霉素结合物（7）和DPCC（10）孵育72小时后，没有抑制正常肾脏LLCPK细胞的增殖，但对CCRF-CEM（分别为73％和41％）和SKOV-3（分别为55％和30％）细胞具有细胞毒性，而Dox具有细胞毒性（60-79％）在所有三种细胞系中都处于相似的条件下，表明这些化合物对癌细胞具有选择性。
• Preparation of a TK/GCV administration system mediated by transferrin modified pro-cationic liposomes
  作者：Zhong, Zhi-Rong、Zhang, Zhi-Rong、Deng, Yong、Liu, Ji、Song, Qing-Guo、Liu, Jie、He, Qin

  DOI：10.1691/ph.2007.7.6248

  日期：——

  Transferrin modified pro-cationic liposomes were prepared and used to investigate the effect of targeting therapeutic genes to human hepatoma carcinoma cells in vitro. The main lipid CHETA, cholest-5-en-3β-yl[2-[[4-[(carboxymethyl)dithio]-1-iminobutyl]amino]ethyl] carbamate (C36H61N3O4S2), was synthesized and used to prepare pro-cationic liposomes. The thymidine kinase (TK) gene loaded pro-cationic liposomes were prepared by first mixing the plasmid DNA and protamine together, and then incubating the resulted polyplexes with blank pro-cationic liposomes preformed by the thin film dispersion-sonication method. Transferrin (Tf) was adsorbed on the surface of pro-cationic liposomes via electrostatic interactions to form transferrin modified pro-cationic liposomes. Cellular association was measured by fluorimetry at excitation and emission wavelengths of 490 and 520 nm, respectively. The viability of TK gene infected cells following administration of ganciclovir (GCV) was investigated by MTT assay. The transferrin modified TK gene pro-cationic liposomes had a mean diameter of 240 ± 12 nm and zeta potential of –24.10 ± 2.5 mV (n = 3). The transmission electron microscopy image indicated that most of the liposomes were relatively regular and spherical with a condensed core inside. Cell-associated fluorescence of Tf-liposomes and unmodified liposomes (without transferrin) was 7.8 × 106, and 3.2 × 106 per milligram protein, respectively. Compared to LipofectamineTM 2000 (Invitrogen, USA) the pro-cationic liposomes and transferrin modified pro-cationic liposomes had less cytotoxicity to cells. The transduced TK gene HepG2 cells were more sensitive to GCV than the un-transduced TK gene ones and the human normal Chang liver cells were not affected by the TK/GCV system mediated by procationic liposomes.

  转铁蛋白修饰的前阳离子脂质体被制备并用于研究靶向治疗基因对人肝肿瘤细胞的体外效果。主要脂质CHETA、胆固醇-5-烯-3β-基[2-[[4-[(羧甲基)二硫]-1-亚氨基丁基]氨基]乙基]氨基甲酸酯（C36H61N3O4S2）被合成并用于制备前阳离子脂质体。负载胸苷激酶（TK）基因的前阳离子脂质体是通过将质粒DNA与鱼精蛋白混合后，孵育得到的聚复合物与通过薄膜分散-超声法预先形成的空白前阳离子脂质体。转铁蛋白（Tf）通过静电相互作用被吸附在前阳离子脂质体的表面，从而形成转铁蛋白修饰的前阳离子脂质体。细胞结合量通过在490和520 nm的激发和发射波长下进行荧光测定来测量。通过MTT法研究了在施用更昔洛韦（GCV）后，TK基因感染细胞的存活率。转铁蛋白修饰的TK基因前阳离子脂质体的平均直径为240 ± 12 nm，zeta电位为–24.10 ± 2.5 mV（n = 3）。透射电子显微镜图像显示，大多数脂质体相对规则且呈球形，内部有致密的核心。Tf-脂质体和未修饰脂质体（未含转铁蛋白）的细胞结合荧光分别为7.8 × 106和3.2 × 106每毫克蛋白。与LipofectamineTM 2000（Invitrogen, USA）相比，前阳离子脂质体和转铁蛋白修饰的前阳离子脂质体对细胞的细胞毒性较低。转导的TK基因HepG2细胞对GCV的敏感性高于未转导的TK基因细胞，而人正常Chang肝细胞则未受到前阳离子脂质体介导的TK/GCV系统的影响。
• Aptamer protective groups tolerate different reagents and reactions for regioselective modification of neomycin B
  作者：Andreas A. Bastian、Agnieszka Gruszka、Philippe Jung、Andreas Herrmann

  DOI：10.1039/d0ob02104k

  日期：——

  protective group strategy for the one-step regioselective transformation of aminoglycoside antibiotics was found to be compatible with diverse reagents and reaction conditions. New derivatives of neomycin B were synthesized with regioselectivities of >99%. This result extends the scope of applicability of APGs facilitating access to novel aminoglycoside derivatives.

  发现用于氨基糖苷类抗生素一步区域选择性转化的适体保护基策略与多种试剂和反应条件兼容。新霉素 B 的新衍生物合成具有 >99% 的区域选择性。这一结果扩大了 APG 的适用范围，有助于获得新的氨基糖苷类衍生物。