美替沙腙 | 1910-68-5

• 物质功能分类: 化学试剂 - 有机试剂 - 腙
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 美替沙腙
• 中文别名: 肼硫代羰酰胺,2-(1,2-二氢-1-甲基-2-氧代-3H-吲哚-3-亚基)
• 英文名称: metisazone
• 英文别名: methisazone；[(1-methyl-2-oxoindol-3-ylidene)amino]thiourea
• CAS: 1910-68-5
• 化学式: C₁₀H₁₀N₄OS
• mdl: MFCD00170583
• 分子量: 234.282
• InChiKey: DLGSOJOOYHWROO-UHFFFAOYSA-N

物化性质

• 熔点：
  245°
• 沸点：
  410.3±28.0 °C(Predicted)
• 密度：
  1.3101 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.72
• 氢给体数：
  2.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2933790090

SDS

Name:	n-Methylisatin 3-(thiosemicarbazone) 96% Material Safety Data Sheet
Synonym:	Methisazon
CAS:	1910-68-5

Section 1 - Chemical Product MSDS Name:n-Methylisatin 3-(thiosemicarbazone) 96% Material Safety Data Sheet
Synonym:Methisazon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1910-68-5	N-Methylisatin 3-(thiosemicarbazone),		217-616-2

Hazard Symbols: Not available.
Risk Phrases:

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Appearance: Target Organs: None.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits +--------------------+-------------------+-------------------+-----------------+ | Chemical Name | ACGIH | NIOSH |OSHA - Final PELs| |--------------------|-------------------|-------------------|-----------------| | N-Methylisatin 3-(t|none listed |none listed |none listed | | hiosemicarbazone), | | | | | 96% | | | | +--------------------+-------------------+-------------------+-----------------+ OSHA Vacated PELs: N-Methylisatin 3-(thiosemicarbazone), 96%: No OSHA Vacated PELs are listed for this chemical.
Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Appearance: not available
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: @ 760.00mm Hg
Freezing/Melting Point: 235 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
NFPA Rating: Not published.
Explosion Limits, Lower: Not available.
Upper: Not available.
Decomposition Temperature:
Solubility:
Specific Gravity/Density:
Molecular Formula: C10H10N4OS
Molecular Weight: 234.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1910-68-5: NL7960000 LD50/LC50:
CAS# 1910-68-5: Oral, mouse: LD50 = 4 gm/kg.
Carcinogenicity:
N-Methylisatin 3-(thiosemicarbazone), 96% - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Chemical waste generators must determine whether a discarded chemical is classif as a hazardous waste.
US EPA guidelines for the classification determination are listed in 40 CFR Part Additionally, waste generators must consult state and local hazardous waste regu ensure complete and accurate classification.
RCRA P-Series: None listed.
RCRA U-Series: None listed.

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Section 14 - TRANSPORT INFORMATION

CDG/CPL
Not classified as hazardous for supply.
Canadian TDG
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1910-68-5: No information available.
United Kingdom Occupational Exposure Limits
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
WHMIS: Not available.
CAS# 1910-68-5 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 1910-68-5 is not listed on the TSCA inventory.
It is for research and development use only.
Health & Safety Reporting List
None of the chemicals are on the Health & Safety Reporting List.
Chemical Test Rules
None of the chemicals in this product are under a Chemical Test Rule.
Section 12b
None of the chemicals are listed under TSCA Section 12b.
TSCA Significant New Use Rule
None of the chemicals in this material have a SNUR under TSCA.
SARA
Section 302 (RQ)
None of the chemicals in this material have an RQ.
Section 302 (TPQ)
None of the chemicals in this product have a TPQ.
Section 313
No chemicals are reportable under Section 313.
Clean Air Act:
This material does not contain any hazardous air pollutants.
This material does not contain any Class 1 Ozone depletors.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  lead(II) nitrate 、 美替沙腙 在 sodium acetate 作用下， 以 水 、 丙酮 为溶剂， 生成 {Pb(C10H9N4OS)2}
  参考文献：
  名称：

  Hovorka, H.; Holzbecher, Z., Collection of Czechoslovak Chemical Communications, 1949, vol. 14, p. 248 - 262

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘苯胺 在 盐酸 、 甲基锂 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 43.67h， 生成 美替沙腙
  参考文献：
  名称：

  钯催化双羰基化方法从 2-碘苯胺制备靛红

  摘要：

  已开发出合成靛红的高产程序。用接近化学计量的 CO 对 2-碘苯胺进行连续 Pd 催化双羰基化，然后进行酸促进环化，很容易得到一系列靛红。发现 2-碘苯胺以良好到极好的产率转化为靛红，具有良好的官能团耐受性。该协议证明适用于靛红的 13C 同位素标记, 并扩展到 13C 同位素标记的抗病毒药物美替沙宗和实验性抗精神分裂症药物 ML137 的合成。

  DOI：

  10.1002/ejoc.201600143

文献信息

• Synthesis, Anticancer and Antibacterial Activity of Some Novel Mononuclear Ru(II) Complexes
  作者：Upal Kanti Mazumder、Malaya Gupta、Subhas Somalingappa Karki、Shiladitya Bhattacharya、Suresh Rathinasamy、Sivakumar Thangavel

  DOI：10.1248/cpb.52.178

  日期：——

  In search of potential anticancer drug candidates in ruthenium complexes, a series of mononuclear ruthenium complexes of the type [Ru(phen)2(nmit)]Cl2 (Ru1), [Ru(bpy)2(nmit)]Cl2 (Ru2), [Ru(phen)2(icpl)]Cl2 (Ru3), Ru(bpy)2(icpl)]Cl2 (Ru4) (phen=1,10-phenanthroline; bpy=2,2′-bipyridine; nmit=N-methyl-isatin-3-thiosemicarbazone, icpl=isatin-3-(4-Cl-phenyl)thiosemicarbazone) and [Ru(phen)2(aze)]Cl2 (Ru5), [Ru(bpy)2(aze)]Cl2 (Ru6) (aze=acetazolamide) and [Ru(phen)2(R-tsc)](ClO4)2 (R=methyl (Ru7), ethyl (Ru8), cyclohexyl (Ru9), 4-Cl-phenyl (10), 4-Br-phenyl (Ru11), and 4-EtO-phenyl (Ru12), tsc=thiosemicarbazone) were prepared and characterized by elemental analysis, FTIR, 1H-NMR and FAB-MS. Effect of these complexes on the growth of a transplantable murine tumor cell line (Ehrlich Ascites Carcinoma) and their antibacterial activity were studied. In cancer study the effect of hematological profile of the tumor hosts have also been studied. In the cancer study, the complexes Ru1—Ru4, Ru10 and Ru11 have remarkably decreased the tumor volume and viable ascitic cell count as indicated by trypan blue dye exclusion test (p<0.05). Treatment with the ruthenium complexes prolonged the lifespan of Ehrlich Ascites Carcinoma (EAC) bearing mice. Tumor inhibition by the ruthenium chelates was followed by improvements in hemoglobin, RBC and WBC values. All the complexes showed antibacterial activity, except Ru5 and Ru6. Thus, the results suggest that these ruthenium complexes have significant antitumor property and antibacterial activity. The results also reflect that the drug does not adversely affect the hematological profiles as compared to that of cisplatin on the host.

  为了寻找潜在的抗癌药物候选物，合成并表征了一系列单核钌配合物，包括[Ru(phen)2(nmit)]Cl2 (Ru1)、[Ru(bpy)2(nmit)]Cl2 (Ru2)、[Ru(phen)2(icpl)]Cl2 (Ru3)、[Ru(bpy)2(icpl)]Cl2 (Ru4)（其中phen=1,10-菲咯啉，bpy=2,2'-联吡啶，nmit=N-甲基-异氮茚-3-缩氨基硫脲，icpl=异氮茚-3-(4-氯苯基)缩氨基硫脲），以及[Ru(phen)2(aze)]Cl2 (Ru5)、[Ru(bpy)2(aze)]Cl2 (Ru6)（aze=醋唑磺胺）和[Ru(phen)2(R-tsc)](ClO4)2（R=甲基(Ru7)、乙基(Ru8)、环己基(Ru9)、4-氯苯基(Ru10)、4-溴苯基(Ru11)和4-乙氧基苯基(Ru12)，tsc=缩氨基硫脲）。研究了这些配合物对可移植的小鼠肿瘤细胞系（埃利希腹水癌）生长的影响及其抗菌活性。在癌症研究中，还研究了肿瘤宿主血液学特征的影响。在癌症研究中，配合物Ru1—Ru4、Ru10和Ru11显著减少了肿瘤体积和活腹水细胞数量，通过台阶蓝染色排斥试验显示（p<0.05）。使用这些钌配合物治疗延长了携带埃利希腹水癌（EAC）小鼠的寿命。钌配合物抑制肿瘤后，血红蛋白、红细胞和白细胞值有所改善。所有配合物都显示出抗菌活性，除了Ru5和Ru6。因此，结果表明这些钌配合物具有显著的抗肿瘤特性和抗菌活性。结果还反映出，与顺铂相比，该药物对宿主的血液学特征没有负面影响。
• Coordination compounds of copper(II), nickel(II), and cobalt(II) with β-thiosemicarbazones of isatin and N-methylisatin
  作者：N. M. Samus’、V. I. Tsapkov、A. P. Gulya

  DOI：10.1007/s11176-005-0026-3

  日期：2004.9

  Isatin thiosemicarbazone (HL) reacts in aquoeus-ethanolic medium with copper(II) chloride and bromide (pH 7–7.5, ethanolic KOH) to give coordination compounds CuLX⋅nH2O (X = Cl, Br; n = 3, 4). In the presence of amines (A = C5H5N, 3-CH3C5H4N, and 4-CH3C5H4N), complexes CuALX⋅2H2O and CuA2LX⋅H2O (X = Cl, Br) are formed. With nickel(II) or cobalt(II) chlorides, thiosemicarbazone HL, and pyridine (1:1:3) as starting compounds, compounds MPy2LCl⋅H2O (M = Ni, Co) are isolated. Under similar conditions, N-methylisatin β-thiosemicarbazone (HL’) reacts with chlorides of the above-noted metals in the presence of pyridine to give complexes MPy2L’Cl⋅H2O (M = Cu, Ni, Co). All the complexes are monomeric and have a pseudooctahedral structure of the coordination unit. Thiosemicarbazones HL and HL′ in these complexes behave as tridentate monodeprotonated O,N,S-ligands. Thermolysis of these substances passes through the stages of dehydration (60–90°C), deaquation (135–140°C) or deamination (160–215°C), and complete thermal decomposition (560–670°C).

  异香豆素硫脲（HL）在水-乙醇介质中与氯化铜(II)和溴化铜(II)（pH 7–7.5，乙醇氢氧化钾）反应，生成配合物CuLX⋅n （X = Cl, Br; n = 3, 4）。在胺类（A = C5H5N, 3-CH3C5H4N和4-CH3C5H4N）存在下，形成络合物CuALX⋅2 和CuA2LX⋅H2O（X = Cl, Br）。使用氯化镍(II)或氯化钴(II)，硫脲HL和吡啶（1:1:3）作为起始化合物，分离出化合物MPy2LCl⋅ （M = Ni, Co）。在类似条件下，N-甲基异香豆素β-硫脲（HL'）在吡啶存在下与上述金属的氯化物反应，生成络合物MPy2L'Cl⋅ （M = Cu, Ni, Co）。所有络合物均为单体，并具有伪八面体的配位单元结构。这些络合物中的硫脲HL和HL'表现为三齿单去质子化的O,N,S-配体。这些物质的热分解经历脱水（60–90°C），去水合（135–140°C）或脱胺反应（160–215°C），以及完全热分解（560–670°C）的阶段。
• Microwave‐assisted synthesis and antimicrobial activity of novel spiro 1,3,4‐thiadiazolines from isatin derivatives
  作者：Daniel Pereira Costa、Aleff Cruz Castro、Girlyanderson Araújo Silva、Claudio Gabriel Lima‐Junior、Francisco Patricio Andrade Júnior、Edeltrudes Oliveira Lima、Boniek Gontijo Vaz、Lidya Cardoso Silva

  DOI：10.1002/jhet.4213

  日期：2021.3

  This work describes the synthesis of spiro 1,3,4‐thiadiazolines from isatin‐β‐thiosemicarbazone acetylation, using microwave irradiation as a source of heating the reaction medium. N‐substituted isatin derivatives were used as substrates to obtain thiosemicarbazones by adding thiosemicarbazide to the isatin ketone carbonyl. The final synthetic step was the reaction of thiosemicarbazones with acetic

  这项工作描述了由Isatin-β-thiosemicarbazone乙酰化反应合成螺1,3,4-噻二唑啉，利用微波辐射作为加热反应介质的来源。ñ通过将thiosemicarbazide添加到isatin ketone羰基上，使用预先取代的isatin衍生物作为底物来获得thiosemicarbazones。最终的合成步骤是在微波辐射下硫代半氨基甲酮与乙酸酐的反应，得到螺环化合物。反应时间为6至18分钟，收率高达90％。生物学测定显示出有希望的抗菌和抗真菌活性，尤其是衍生自烯丙基化的靛红的螺噻二唑啉。根据计算机研究的结果，所有提出的分子均被证明是潜在的候选药物，并且符合Lipinski规则，具有令人满意的相似性和评分。微波反应器的使用对于合成硫半脲和螺环化合物非常有效，从而大大减少了常规加热的反应时间。考虑到抗药性的威胁，这项工作提出了一系列易于通过微波反应获得的生物活性分子。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C2, 7.16, page 752 - 756
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Hg: MVol.A2, 120, page 875 - 876
  作者：

  DOI：——

  日期：——