O-neopentylthioxocarbamate | 175725-53-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: O-neopentylthioxocarbamate
• 英文别名: thiocarbamic acid O-neopentyl ester；Thiocarbamidsaeure-O-neopentylester；Neopentylxanthogenamid；O-neopentyl thiocarbamate；O-(2,2-dimethylpropyl) carbamothioate
• CAS: 175725-53-8
• 化学式: C₆H₁₃NOS
• mdl: MFCD19205125
• 分子量: 147.241
• InChiKey: ITWWAVWXPBKUBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-neopentylthioxocarbamate 、 溴乙酸 在 苯 作用下， 生成 neopentyloxycarboximidoylmercapto-acetic acid ; hydrobromide
  参考文献：
  名称：

  Aggressive Metastatic Follicular Thyroid Carcinoma with Anaplastic Transformation Arising from a Long-Standing Goiter in a Patient with Pendred's Syndrome

  摘要：

  In this article we describe detailed pathological and molecular genetics studies in a consanguineous kindred with Pendred's syndrome. The index patient was a 53-year-old female patient with congenital deafness and goiter. Her parents were first-degree cousins. She had a large goiter (150 g) that had been present since childhood. One of her sisters and a niece are also deaf and have goiter as well. The presence of Pendred's syndrome was confirmed by a positive perchlorate test and the demonstration of a Mondini malformation. Thyroid function tests (under levothyroxine [LT4] therapy) were in the euthyroid range with a thyrotropin [TSH] level of 2.8 muU/mL (0.2-3.2), a serum total thyroxine (T-4) of 90 nmol/L (54-142), and a serum total triiodothyronine (T-3) of 2.7 nmol/L (0.8-2.4). Total thyroidectomy was performed, and the mass in the right lobe was found to have invaded adjacent tissues. The histopathological findings were consistent with a follicular carcinoma with areas of anaplastic transformation and lung metastasis. The patient was treated twice with 100 mCi (131)iodine (3,700 MBq) and received suppressive doses of LT4. Postoperatively, the serum thyroglobulin (Tg) levels remained markedly elevated (2,352 to 41,336 ng/mL). The patient died of a sudden severe episode of hemoptysis. Sequence analysis of the PDS gene performed with DNA from the two relatives with Pendred's syndrome revealed the presence of a deletion of thymidine 279 in exon 3, a point mutation that results in a frameshift and a premature stop codon at codon 96 in the pendrin molecule. We concluded that prolonged TSH stimulation because of iodine deficiency or dyshormonogenesis in combination with mutations of oncogenes and/or tumor suppressor genes, may result in the development of follicular thyroid carcinomas that undergo transformation into anaplastic cancers. It is likely that these pathogenetic mechanisms have been involved in the development of aggressive metastatic thyroid cancer in this unusual patient with Pendred's syndrome.

  DOI：

  10.1089/105072501753211073
• 作为产物：
  描述：

  neopentyl N-toluenesulfonyl thioxocarbamate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以90%的产率得到O-neopentylthioxocarbamate
  参考文献：
  名称：

  自由基反应的发明。第XXXV部分。N-磺酰基硫代氨基甲酸酯的新型自由基裂变反应

  摘要：

  描述了从醇与甲磺酰基-和甲苯磺酰基异硫氰酸酯的反应获得的N-磺酰基硫代氨基甲酸酯的新的自由基裂变反应，得到相应的O-烷基硫代氨基甲酸酯。

  DOI：

  10.1016/0040-4020(95)01019-x

文献信息

• Johansson, Arkiv foer Kemi, 1946, vol. 22 B, # 2, p. 4
  作者：Johansson

  DOI：——

  日期：——
• The invention of radical reactions. Part XXXV. A novel radical fission reaction of N-sulfonylthioxocarbamates
  作者：Derek H.R. Barton、Giovanni Fontana、Yun Yang

  DOI：10.1016/0040-4020(95)01019-x

  日期：1996.2

  A novel radical fission reaction of N-sulfonylthioxocarbamates, obtained from the reactionof alcohols with methanesulfonyl- and toluenesulfonyl isothiocyanates, to give the corresponding O-alkylthioxocarbamates, is described.

  描述了从醇与甲磺酰基-和甲苯磺酰基异硫氰酸酯的反应获得的N-磺酰基硫代氨基甲酸酯的新的自由基裂变反应，得到相应的O-烷基硫代氨基甲酸酯。
• Aggressive Metastatic Follicular Thyroid Carcinoma with Anaplastic Transformation Arising from a Long-Standing Goiter in a Patient with Pendred's Syndrome
  作者：Rosalinda Camargo、Eduardo Limbert、Mary Gillam、Maria Manuela Henriques、Carlos Fernandes、Ana Luisa Catarino、Jorge Soares、Venancio A.F. Alves、Peter Kopp、Geraldo Medeiros-Neto

  DOI：10.1089/105072501753211073

  日期：2001.10

  In this article we describe detailed pathological and molecular genetics studies in a consanguineous kindred with Pendred's syndrome. The index patient was a 53-year-old female patient with congenital deafness and goiter. Her parents were first-degree cousins. She had a large goiter (150 g) that had been present since childhood. One of her sisters and a niece are also deaf and have goiter as well. The presence of Pendred's syndrome was confirmed by a positive perchlorate test and the demonstration of a Mondini malformation. Thyroid function tests (under levothyroxine [LT4] therapy) were in the euthyroid range with a thyrotropin [TSH] level of 2.8 muU/mL (0.2-3.2), a serum total thyroxine (T-4) of 90 nmol/L (54-142), and a serum total triiodothyronine (T-3) of 2.7 nmol/L (0.8-2.4). Total thyroidectomy was performed, and the mass in the right lobe was found to have invaded adjacent tissues. The histopathological findings were consistent with a follicular carcinoma with areas of anaplastic transformation and lung metastasis. The patient was treated twice with 100 mCi (131)iodine (3,700 MBq) and received suppressive doses of LT4. Postoperatively, the serum thyroglobulin (Tg) levels remained markedly elevated (2,352 to 41,336 ng/mL). The patient died of a sudden severe episode of hemoptysis. Sequence analysis of the PDS gene performed with DNA from the two relatives with Pendred's syndrome revealed the presence of a deletion of thymidine 279 in exon 3, a point mutation that results in a frameshift and a premature stop codon at codon 96 in the pendrin molecule. We concluded that prolonged TSH stimulation because of iodine deficiency or dyshormonogenesis in combination with mutations of oncogenes and/or tumor suppressor genes, may result in the development of follicular thyroid carcinomas that undergo transformation into anaplastic cancers. It is likely that these pathogenetic mechanisms have been involved in the development of aggressive metastatic thyroid cancer in this unusual patient with Pendred's syndrome.