硝基胍 | 556-88-7

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 硝基胍
• 中文别名: 橄苦岩；苦橄岩；硝基亚胺脲
• 英文名称: nitroguanidine
• 英文别名: 1-nitroguanidine；Nitroguanidine
• CAS: 556-88-7
• 化学式: CH₄N₄O₂
• mdl: MFCD00007039
• 分子量: 104.068
• InChiKey: IDCPFAYURAQKDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  239 °C (dec.) (lit.)
• 沸点：
  195.15°C (rough estimate)
• 密度：
  1.55g/cm3
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）
• LogP：
  -0.815 at 20℃
• 物理描述：
  Nitroguanidine, [dry] appears as a yellow solid in the form of crystalline needles. Decomposes at 480°F and emits toxic oxides of nitrogen. May explode under exposure to intense heat or fire. Primary hazard is blast of explosion, not flying projectiles or fragments .
• 颜色/状态：
  Needles, prisms from water /alpha 1-Nitroguanidine/
• 蒸汽压力：
  1.43X10-11 mm Hg at 25 °C
• 亨利常数：
  Henry's Law constant = 4.45X10-16 atm cu m/mol at 25 °C
• 稳定性/保质期：
  1. 稳定性：稳定。 2. 禁配物：强氧化剂、强碱。 3. 应避免接触的条件：热、摩擦、震动及撞击。 4. 聚合危害：不聚合。 5. 分解产物：氮氧化物、氨。
• 分解：
  It decomposes at 480 °F and emits toxic oxides of nitrogen. /Nitroguanidine, dry/

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

硝基胍（NG）是军用推进剂和弹药的一个组成部分，在大鼠中对其代谢和处置进行了研究。放射性标记的硝基胍（(14C)NG）通过口服给药20和200毫克/千克，以及静脉给药20毫克/千克。无论给药途径如何，所有动物在给药后48小时内尿液中的放射性标记物都被定量回收。尿液色谱分析表明，(14C)NG以原形排出；处理过的动物的呼出空气、粪便或组织中没有发现放射性标记。在NG的处置中没有观察到性别差异。(14C)NG在大剂量动物血液中的动力学被追踪。NG的消除半衰期约为2小时。口服给药的NG的生物利用度为100%；血液中NG的动力学与剂量无关。口服NG后1小时检查组织，发现NG在体内均匀分布。硝基胍是一种低毒化学品（LD50大于5克/千克）；它从胃肠道被定量吸收，分布到全身，并迅速通过尿液排出。

The metabolism and disposition of nitroguanidine (NG), a component of military propellants and munitions, were examined in the rat. Radiolabeled nitroguanidine ((14C)NG) was administered orally at doses of 20 and 200 mg/kg and intravenously at a dose of 20 mg/kg. Regardless of the route of administration, the radiolabel was recovered quantitatively in the urine of all animals within 48 hr after dosing. Chromatographic analysis of the urine indicated that the (14C)NG was excreted unchanged; no radiolabel was found in the expired air, feces, or tissues of the treated animals. No sex differences were seen in the disposition of NG. The kinetics of (14C)NG in the blood of the dosed animals was followed. The elimination half-life of NG was on the order of 2 hr. The bioavailability of orally administered NG was 100%; the kinetics of NG in the blood was not dose dependent. Examination of tissues 1 hr after an oral dose of NG showed that NG was evenly distributed throughout the body. Nitroguanidine is a chemical of low toxicity (LD50 greater than 5 g/kg); it is quantitatively absorbed from the gastrointestinal tract, distributed throughout the body, and rapidly excreted in the urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

尿液中含有硝基胍，这是大鼠口服1-甲基-3-硝基-1-亚硝基胍后产生的代谢物。

Urine contained nitroguanidine, a metabolite, resulting from oral admin of 1-methyl-3-nitro-1-nitrosoguanidine to rats.

来源:Hazardous Substances Data Bank (HSDB)

代谢

尼奥尼克丁类杀虫剂是最新的一类主要杀虫剂，其中的硝基胍或硝基甲烯基团对于在昆虫烟酸受体上的活性以及在相对于哺乳动物受体上的选择性至关重要。最近发现醛氧化酶（AOX）是哺乳动物肝脏中imidacloprid硝基还原酶，能够产生硝基亚胍和胍胺代谢物。本研究考虑了从兔肝部分纯化的AOX还原五种商业硝基胍（即imidacloprid、thiamethoxam、clothianidin和dinotefuran）和硝基甲烯（即nitenpyram）尼奥尼克丁杀虫剂以及三种衍生物（即imidacloprid的N-甲基和硝基甲烯类似物以及desmethylthiamethoxam）的能力。使用LC/MS/MS证明AOX将硝基胍还原为硝基亚胍和胍胺，而硝基甲烯仅还原为相应的硝基亚代谢物。此外，发现硝基亚硝吡胺会自发脱水形成2-腈胍代谢物，模仿主要的光反应。AOX的底物特异性如下：带有三级氮的尼奥尼克丁（N-甲基imidacloprid和thiamethoxam）是差的底物；硝基胍的代谢速度比硝基甲烯快；clothianidin是最快被还原的。在两个浓度的AOX中测量了三种硝基胍还原的动力学常数。在2 mg蛋白/mL时，仅检测到硝基亚代谢物，clothianidin、imidacloprid和dinotefuran的Km值分别为1.03、2.99和2.41 mM，Vmax值分别为5.13、2.54和0.98 nmol/min/mg蛋白。在5 mg蛋白/mL时，检测到氨基和硝基亚代谢物。然而，对于每种硝基胍，在底物水平高达4 mM时，硝基亚代谢物的形成并未饱和，而氨基代谢物形成的Km值分别为0.052、0.16和0.084 mM，对应的Vmax值分别为0.80、1.24和0.79 nmol/min/mg蛋白，对于clothianidin、imidacloprid和dinotefuran。这些体外观察显示了AOX催化还原速率在结构上的巨大差异，有助于解释对尼奥尼克丁杀虫剂体内代谢的广泛研究。

The nitroguanidine or nitromethylene moiety of the newest major class of insecticides, the neonicotinoids, is important for potency at insect nicotinic receptors and selectivity relative to mammalian receptors. Aldehyde oxidase (AOX) was recently identified as the imidacloprid nitroreductase of mammalian liver, producing both nitrosoguanidine and aminoguanidine metabolites. /This/ study considers the ability of AOX, partially purified from rabbit liver, to reduce five commercial nitroguanidine (i.e., imidacloprid, thiamethoxam, clothianidin, and dinotefuran) and nitromethylene (i.e., nitenpyram) neonicotinoid insecticides and three derivatives thereof (i.e., the N-methyl and nitromethylene analogues of imidacloprid and desmethylthiamethoxam). LC/MS/MS was used to demonstrate that AOX reduces nitroguanidines to both nitroso- and aminoguanidines, while nitromethylenes are reduced only to the corresponding nitroso metabolites. Additionally, nitrosonitenpyram was found to spontaneously dehydrate to form a 2-cyanoamidine metabolite, mimicking a predominant photoreaction. The substrate specificity of AOX was characterized as follows: Neonicotinoids with a tertiary nitrogen (N-methylimidacloprid and thiamethoxam) are poor substrates; nitroguanidines are metabolized faster than nitromethylenes; and clothianidin is the most rapidly reduced. Kinetic constants were measured for reduction of three nitroguanidines at two concentrations of AOX. At 2 mg protein/mL, only nitroso metabolites were detected, with Km values of 1.03, 2.99, and 2.41 mM and Vmax values of 5.13, 2.54, and 0.98 nmol/min/mg protein measured for clothianidin, imidacloprid, and dinotefuran, respectively. At 5 mg protein/mL, both amino and nitroso metabolites were detected. However, with each nitroguanidine, the formation of nitroso metabolites did not saturate at substrate levels up to 4 mM, whereas amino metabolite formation exhibited Km values of 0.052, 0.16, and 0.084 mM with corresponding Vmax values of 0.80, 1.24, and 0.79 nmol/min/mg protein for clothianidin, imidacloprid, and dinotefuran, respectively. These in vitro observations show large structural differences in the rates of AOX-catalyzed reduction and help to interpret the extensive studies on in vivo metabolism of neonicotinoid insecticides.

来源:Hazardous Substances Data Bank (HSDB)

代谢

咪唑虫吡啶（IMI）既可以通过细胞色素P450酶进行氧化代谢，也可以在硝基胍部分通过胞浆中的“新型烟碱类硝基还原酶”进行还原... . 在将IMI与兔肝胞浆一起孵化时，可以检测到两种主要代谢物：硝基亚胺（IMI-NO）和氨基亚胺（IMI-NH2）。三方面的证据表明，钼-黄素酶乙醛氧化酶（AOX，EC 1.2.3.1）是新型烟碱类硝基还原酶。首先，传统的AOX电子供体底物（苯甲醛、2-羟基嘧啶和N-甲基烟酰胺）显著提高了IMI代谢物形成的速率。别嘌呤醇和敌草快也是有效的电子供体，而NADPH和黄嘌呤则不是。其次，当使用N-甲基烟酰胺作为电子供体时，AOX抑制剂（氰化钾、甲萘醌和马来酸氯苯那敏）会抑制代谢物形成。在没有添加电子供体的情况下，兔肝胞浆仅以较慢的速率将IMI还原为IMI-NO。这种还原也会被氰化钾、甲萘醌和马来酸氯苯那敏抑制，以及额外的AOX抑制剂，如西咪替丁和氯丙嗪。最后，AOX对IMI的硝基还原对有氧环境敏感，但程度远低于细胞色素P450 2D6。在肝胞浆对IMI的硝基还原活性方面，观察到较大的物种差异。虽然兔和猴子（食蟹猴）产生总代谢物水平最高，但人、小鼠、牛和大鼠也迅速代谢IMI。相比之下，狗、猫和鸡的肝胞浆不会以明显的速率还原IMI。作为新型烟碱类硝基还原酶的AOX，可能会限制IMI以及可能的其他新型烟碱类化合物在哺乳动物体内的持久性。

Imidacloprid (IMI) is both oxidatively metabolized by cytochrome P450 enzymes and reduced at the nitroguanidine moiety by a ... cytosolic "neonicotinoid nitroreductase" ... . Two major metabolites are detected on incubation of IMI with rabbit liver cytosol: the nitrosoguanidine (IMI-NO) and the aminoguanidine (IMI-NH2). Three lines of evidence identify the molybdo-flavoenzyme aldehyde oxidase (AOX, EC 1.2.3.1) as the neonicotinoid nitroreductase. First, classical AOX electron donor substrates (benzaldehyde, 2-hydroxypyrimidine, and N-methylnicotinamide) dramatically increase the rate of formation of IMI metabolites. Allopurinol and diquat are also effective electron donors, while NADPH and xanthine are not. Second, AOX inhibitors (potassium cyanide, menadione, and promethazine) inhibit metabolite formation when N-methylnicotinamide is utilized as an electron donor. Without the addition of an electron donor, rabbit liver cytosol reduces IMI only to IMI-NO at a slow rate. This reduction is also inhibited by potassium cyanide, menadione, and promethazine, as well as by additional AOX inhibitors, cimetidine and chlorpromazine. Finally, IMI nitroreduction by AOX is sensitive to an aerobic atmosphere, but to a much lesser extent than cytochrome P450 2D6. Large species differences are observed in the IMI nitroreductive activity of liver cytosol. While rabbit and monkey (Cynomolgus) give the highest levels of total metabolite formation, human, mouse, cow, and rat also metabolize IMI rapidly. In contrast, dog, cat, and chicken liver cytosols do not reduce IMI at appreciable rates. AOX, as a neonicotinoid nitroreductase, may limit the persistence of IMI, and possibly other neonicotinoids, in mammals.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：D；无法归类为人类致癌性。分类依据：在现有文献中未找到关于致癌性的相关数据。人类致癌性数据：无。动物致癌性数据：无。/基于先前的分类系统/

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Pertinent data regarding carcinogenicity have not been located in the available literature. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: None. /Based on former classification system/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

立即急救：确保已经进行了充分的中毒物清洗。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或置于左侧卧位（如果可能的话，头部向下）以保持呼吸道畅通，防止误吸。保持患者安静，维持正常体温。寻求医疗帮助。/二硝基酚及其相关化合物/

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Dinitrophenol and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非重复呼吸面罩以10至15升/分钟的速度给予氧气。监测休克并如有必要进行治疗……监测肺水肿并如有必要进行治疗……预期癫痫发作并如有必要进行治疗……对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……在去污染后，用干燥的无菌敷料覆盖皮肤烧伤……在体温过高的情况下，可能需要快速身体降温。水杨酸类药物是禁忌的。/二硝基酚及其相关化合物/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination. flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . Rapid body cooling may be necessary in case of hyperthermia. Salicylates are contraindicated. /Dinitrophenol and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿...监测心率和必要时治疗心律失常...开始静脉输注0.9%生理盐水（NS）或乳酸林格氏液（LR）/SRP：“保持开放”，最低流速/。对于脱水和低血压伴有低血容量的迹象，谨慎给予液体。如果病人在正常液体容量下出现低血压，考虑使用血管加压药。注意液体过载的迹象...用地西泮或劳拉西泮治疗癫痫...如果病人在严重低氧血症、发绀和心脏损害（对氧气无反应）出现症状，给予1%亚甲基蓝溶液...使用丙美卡因氢氯化物协助眼部冲洗.../二硝基酚及其相关化合物/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of 0.9% saline (NS) or lactated Ringer's (LR) /SRP: "To keep open", minimal flow rate/. For dehydration and hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dinitrophenol and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：亚慢性或预慢性暴露/ 对硝基胍的90天亚慢性口服毒性在雄性和雌性Sprague-Dawley大鼠中进行评估。硝基胍以0、100、316和1000毫克/千克/天的剂量水平通过饮食给药，持续90天。每个性别/剂量组有15只动物。在饮食中添加硝基胍一致性地减少了食物摄入量，并显著（p<=0.05）增加了水的摄入量。在研究期间的13周中有5周观察到雌性高剂量组的体重增长显著（p<=0.05）减少。在研究期间没有观察到其他可归因于测试化合物的临床体征。在尸检时采集的血液样本进行血液学和血清化学分析，没有显示显著异常，可以归因于硝基胍的给药。对对照组和1000毫克/千克/天剂量组动物的组织的显微镜检查没有发现可归因于硝基胍给药的病变。在终末牺牲时，雌性1000毫克/千克/天组的脑重与体重比与对照组相比显著（p<=0.05）增加。基于在5、6、8、9和12周时雌性大鼠在1000毫克/千克/天的生长速率显著降低，NOAEL（无观察到不良效应的剂量水平）为316毫克/千克/天。

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The 90-day subchronic oral toxicity of nitroguanidine was evaluated in male and female Sprague-Dawley rats. Nitroguanidine was administered in the diet at dose levels of 0, 100, 316, and 1000 mg/kg/day for 90 days. There were 15 animals/sex/dose. The addition of nitroguanidine to the diet consistently reduced food consumption and caused significant (p<=0.05) increases in water consumption. Significantly (p<=0.05) reduced weight gains were observed in the female high-dose group for 5 of the 13 weeks of the study period. No other clinical signs attributable to the test compound were observed during the study. Blood samples taken at necropsy for hematological and serum chemistry analyses exhibited no significant abnormalities that could be attributed to nitroguanidine dosing. Microscopic examination of tissues from the control and 1000 mg/kg/day dose group animals revealed no lesions attributable to the administration of nitroguanidine. The female 1000 mg/kg/day group had a significantly (p<=0.05) increased brain-to- body weight ratio compared with that of the controls at terminal sacrifice. Based on a significant decrease in the rate of growth of female rats at 1000 mg/kg/day on weeks 5, 6, 8, 9 and 12, the NOAEL is 316 mg/kg/day.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C标记的硝基脒酸静脉注射给Sprague-Dawley大鼠，剂量为20 mg/kg，通过胃管给药剂量为20 mg/kg，口服给药剂量为200 mg/kg。在给药后5分钟至24小时的时间点采集血液样本，并在给药后大约4、8、24、32和48小时收集尿液样本。动物在治疗后48小时被处死，分析肝脏、心脏、肺、肾脏、脾脏、大脑、睾丸、卵巢和肌肉中的(14)C活性。无论给药途径如何，给药的标记物都会迅速通过尿液排出。大约50%的标记物在给药后4小时出现在尿液中，大约95%在24小时内排出。

(14)C labeled nitroguanidine was administered to Sprague-Dawley rats intravenously at a dose of 20 mg/kg, by gastric intubation at a dose of 20 mg/kg, and by oral intubation at a dose of 200 mg/kg. Blood samples were collected at times from 5 minutes to 24 hours post dosing, and urine samples were collected at approximately 4, 8, 24, 32, and 48 hours after drug administration. The animals were sacrificed at 48 hours post treatment, and liver, heart, lung, kidney, spleen, brain, testes, ovaries, and muscle were analyzed for (14)C activity. The administered label was rapidly excreted in the urine regardless of the route of dosing. Approximately 50 percent of the label was present in the urine at 4 hours post dosing, and approximately 95 percent was excreted by 24 hours.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  1.1D
• 危险品标志：
  F,Xi
• 安全说明：
  S16,S26,S33,S36/37/39,S37/39,S47
• 危险类别码：
  R5,R36/37/38,R11
• WGK Germany：
  1
• 危险品运输编号：
  UN 1336 4.1/PG 1
• 海关编码：
  2925290090
• 危险类别：
  1.1D
• RTECS号：
  MF4600000
• 包装等级：
  I
• 储存条件：
  储存注意事项： - 为安全起见，储存时可加入不少于15%的水作为稳定剂。 - 储存于阴凉、干燥、通风的爆炸品专用库房。 - 远离火种和热源，库温控制在0℃以下。 - 应与氧化剂和碱类分开存放，切忌混储。 - 配备相应品种和数量的消防器材。 - 储区应备有合适的材料收容泄漏物。 - 禁止震动、撞击和摩擦。

SDS

第一部分：化学品名称

制备方法与用途

化学性质

白色结晶。微溶于水，溶于热水、硫酸及硝酸，在一般有机溶剂中的溶解度不大，微溶于甲醇及丙酮，溶于二甲基亚砜和二甲基甲酰胺。

用途

用作炸药原料，并作为农药合成的中间体，例如吡虫啉、啶虫脒。此外，它还可以还原成氨基胍，用于合成治疗心绞痛药物乐可安等。同时，也可用于炸药及无烟水药的配制。

生产方法

由硝酸在硫酸存在下于20℃反应而得。具体步骤是将硝酸胍缓缓加入浓硫酸中，反应温度不超过20℃，加毕放置后倒入冰水中析出硝基胍，过滤并用水洗去酸性物质，最后从沸水中重结晶得到成品，收率可达70%以上。

另一种生产方法同样是通过硝酸胍在浓硫酸存在下脱水生成硝基胍。具体操作为：将280克硝酸胍缓慢加入已冷却的250毫升浓硫酸（相对密度1.84）中，在加入过程中严格控制反应温度不超过20℃，加完后间断搅拌直至均匀无晶体，随后倒入冰水混合物中充分搅拌并过滤，用水洗至中性后再重结晶即得硝基胍。

类别

爆炸物品

毒性分级

中毒

• 急性毒性：
  • 大鼠口服LD50：10200毫克/公斤
  • 小鼠口服LD50：3850毫克/公斤

爆炸物危险特性

高温、震动、撞击或摩擦均可能引发爆炸。

可燃性危险特性

易燃固体，受热分解产生有毒氧化氮气体。

储运特性

轻装轻放；库房需保持通风，并远离明火和高温环境，避免阳光直射。与氧化剂及易燃物分开存放。

灭火剂

雾状水、泡沫

反应信息

• 作为反应物：
  描述：

  硝基胍 在 hydrazine hydrate 作用下， 以 水 为溶剂， 反应 0.25h， 以43.5%的产率得到1-氨基-3-硝基胍
  参考文献：
  名称：

  叠氮基的竞争配位：基于 3-氨基-1-硝基胍的无溶剂无氯初级炸药的合成

  摘要：

  以配位化学战略为指导思想，开发出一种性能优良的新一代起爆药的安全合成方法。基于 3-氨基-1-硝基胍 (ANQ)、金属阳离子 Co(II)、Ni(II) 和高能叠氮化物基团 (N 3 – )，我们创造了两种无溶剂和不含氯，并通过红外、元素分析和单晶 X 射线衍射进一步证实。热稳定性实验表明它们的热分解温度均超过170℃。敏感性试验和爆炸参数模拟表明，2和3具有优良的爆震性能和安全性能。此外，起爆效率测试结果支持2可作为合适的起爆药。

  DOI：

  10.1021/acs.cgd.1c00926
• 作为产物：
  描述：

  亚硝基胍 在 potassium permanganate 、 硝酸 作用下， 生成 硝基胍
  参考文献：
  名称：

  Thiele, Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 136

  摘要：

  DOI：
• 作为试剂：
  描述：

  硝基胍 、 ethyl 2-formyl-3-(2-methoxy-pyridin-4-yl)propionate 在 硝基胍 作用下， 生成 2-nitroamino-5-(2-methoxy-pyridin-4-yl)methyl-4-pyrimidone
  参考文献：
  名称：

  Pyrimidine compounds

  摘要：

  这些化合物是取代嘧啶化合物，是组胺H.sub.2 -拮抗剂。本发明的一种特定化合物是2-[2-(5-二甲氨基甲基)-2-呋喃甲硫基)乙基氨基]-5-(3-吡啶甲基)-4-嘧啶酮。

  公开号：

  US04649141A1

文献信息

• N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase
  申请人：Combs P. Andrew

  公开号：US20070185165A1

  公开（公告）日：2007-08-09

  The present invention is directed to N-hydroxyamidino compounds which are modulators of indoleamine 2,3-dioxygenase (IDO), as well as pharmaceutical compositions thereof and methods of use thereof relating to the treatment of cancer and other diseases.

  本发明涉及N-羟基酰胺基化合物，其为吲哌酮胺2,3-二氧化酶（IDO）的调节剂，以及与之相关的药物组合物和使用方法，用于治疗癌症和其他疾病。
• Heterocyclic compounds
  申请人：Nihon Tokushu Noyaku Seizo K. K.

  公开号：US04742060A1

  公开（公告）日：1988-05-03

  Novel insecticides of the formula ##STR1## in which n is 0 or 1, X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.

  公式为##STR1##的新型杀虫剂，其中n为0或1，X为S，O，##STR2##，Y为N或##STR3##，Z为含氮的5-或6-成员杂环，R至R.sup.9分别代表氢或指定的有机基团。
• Sur la substitution des alcoyl- et arylguanidines par des restes acides
  作者：Eric Junod

  DOI：10.1002/hlca.19520350343

  日期：1952.5.2

  1. La substitution des guanidines alcoylées ou arylées par le chloroformiate de méthyle (effectuée dans l'acétone en présence de NaOH aq. conc.) est totale chez celles qui portent jusqu'à 3 atomes d'hydrogène, à l'exception de la diphénylguanidine asym. – Les nitro-, mono- et dialcoyl-nitro- et monoaryl-cyanoguanidines ont été dicarbométhoxylées. La dicyandiamide elle-même n'est pas acylée dans les

  1.取代甲氧基氯甲酸甲酯的胍基化合物（影响浓NaOH水溶液的浓度）估计总的乙酰胆碱含量约等于3原子的双氢化萘，其余的是diphénylguanidineasym。-二羰基乙氧基上的硝基，单-和二烯丙基-硝基-等单芳基-氰基胍。La dicyandiamideelle-mêmen'est pasacyléedans lesmêmes条件。
• [EN] SUBSTITUTED PYRAZOLE COMPOUNDS AND METHODS OF USING THEM FOR TREATMENT OF HYPERPROLIFERATIVE DISEASES<br/>[FR] COMPOSÉS PYRAZOLE SUBSTITUÉS ET LEURS PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT DE MALADIES HYPERPROLIFÉRATIVES
  申请人：BANTAM PHARMACEUTICAL LLC

  公开号：WO2018102453A1

  公开（公告）日：2018-06-07

  Disclosed are compounds useful, for example, in methods of treating hyperproliferative disorders such as cancer, methods of arresting the cell cycle in cancer cells, methods of inhibiting glutathione synthesis in cancer cells, and associated compounds for use and uses in medicaments. In certain embodiments, the methods, uses and compounds are provided with reference to compounds of the structural formulae (Ia), (Ib), (Ic), (Id) and (Ie), in which R1, L1, L2, Q, L3, R3, L4, R4, L5, and R5 are as described herein. In certain embodiments, compounds disclosed herein are especially active against cancers having a mutant KRAS gene.

  本文披露了一些化合物，例如在治疗高增殖性疾病如癌症的方法中有用，用于阻止癌细胞周期的方法，用于抑制癌细胞中谷胱甘肽合成的方法，以及用于药物中的相关化合物和用途。在某些实施例中，所述方法、用途和化合物参考了结构式(Ia)、(Ib)、(Ic)、(Id)和(Ie)的化合物，其中R1、L1、L2、Q、L3、R3、L4、R4、L5和R5如本文所述。在某些实施例中，本文披露的化合物对具有突变KRAS基因的癌症特别有效。
• Synthesis and antimicrobial studies of novel bis(diamino)thiazoles
  作者：Sreedharan L. Manju、Satyabhama K. C. Devi、Kallikat N. Rajasekharan

  DOI：10.1002/jhet.106

  日期：2009.5

  The synthesis of novel bis(diamino)thiazoles has been achieved by reacting bis(bromoacetyl)benzene and 1-alkyl(or aryl)-3-(N-nitroamidino)thioureas in presence of triethylamine. These new compounds were characterized by spectral analysis and screened for antimicrobial activities. J. Heterocyclic Chem., 46, 455 (2009).

  通过使双（溴乙酰基）苯与1-烷基（或芳基）-3-（N-硝基酰胺基）硫脲在三乙胺存在下反应，已经实现了新型双（二氨基）噻唑的合成。这些新化合物通过光谱分析进行表征，并筛选抗微生物活性。J.杂环化​​学。，46，455（2009）。

表征谱图